5408-74-2

Basic information

• Product Name: 5-ETHYL-2-VINYL PYRIDINE
• Synonyms: 5-ETHYL-2-VINYL PYRIDINE;PYRIDINE, 2-ETHENYL-5-ETHYL-;3-ethyl-6-vinylpyridine;5-ethyl-2-vinyl-pyridin;2-Vinyl-5-ethylpyridine;2-ethenyl-5-ethylpyridine;2-ethenyl-5-ethyl-pyridine;NSC 8395
• CAS NO: 5408-74-2
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• EINECS: 226-475-6
• Product Categories: Aromatics;Heterocycles;Miscellaneous Reagents
• Mol File: 5408-74-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 235.73°C (rough estimate)
• Flash Point: 76.2 ºC
• Appearance: /
• Density: 1.0050 (rough estimate)
• Vapor Pressure: 0.307mmHg at 25°C
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: 5.15±0.10(Predicted)
• CAS DataBase Reference: 5-ETHYL-2-VINYL PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ETHYL-2-VINYL PYRIDINE(5408-74-2)
• EPA Substance Registry System: 5-ETHYL-2-VINYL PYRIDINE(5408-74-2)

Safety Data

• RIDADR: 2810
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 5408-74-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Oil

Uses

Different sources of media describe the Uses of 5408-74-2 differently. You can refer to the following data:
1. Copolymer, synthesis.
2. 5-Ethyl-2-vinylpyridine (cas# 5408-74-2) is a compound useful in organic synthesis.

InChI:InChI=1/C9H11N/c1-3-8-5-6-9(4-2)10-7-8/h4-7H,2-3H2,1H3

Synthetic route

5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione (646519-88-2) → 5-ethyl-2-vinyl-pyridine (5408-74-2) + Pioglitazone (105355-27-9) + 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (74772-78-4)

Conditions	Yield
With acetic acid; zinc In ethyl acetate at 25 - 35℃; for 9h; Product distribution / selectivity;	A n/a B 41% C n/a
With acetic acid; zinc at 25 - 30℃; for 15h;	A 10% B 25% C 12%
Stage #1: 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione With acetic acid; zinc at 5 - 30℃; for 15h; Stage #2: With sodium carbonate In water; acetic acid Product distribution / selectivity;	A 10% B 20% C 12%

5-ethyl-2-methyl-pyridine (104-90-5) + formaldehyd (50-00-0) → 5-ethyl-2-vinyl-pyridine (5408-74-2) + 5-ethyl-2-(2-hydroxyethyl)pyridine (5223-06-3)

Conditions	Yield
With dipotassium peroxodisulfate; ethanol at 220℃;
In water at 155℃; under 4500.45 Torr; for 4h; Pressure; Autoclave;	A n/a B 70 g

5-ethyl-2-(2-hydroxyethyl)pyridine (5223-06-3) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
With aluminum oxide at 420℃;
With potassium hydroxide at 175℃; Erhitzen unter vermindertem Druck;
With potassium hydroxide Heating; Yield given;

hydrogenchloride (7647-01-0) + 5-ethyl-2-(2-hydroxyethyl)pyridine (5223-06-3) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
at 160 - 170℃; nachfolgenden Erwaermen mit Natronlauge;

5-ethyl-2-<β-oxy-ethyl>-pyridine → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
With hydrogenchloride at 160 - 170℃; im Rohr; Erwaermen mit Natronlauge;
With hydrogenchloride at 160 - 170℃; im Rohr; Destillieren ueber Kaliumhydroxyd;

5-ethyl-2-(2-hydroxyethyl)pyridine (5223-06-3) + potassium hydroxide → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Destillation;

5-ethyl-2-methyl-pyridine (104-90-5) + pyridine-homologous/ues → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: formic acid, tert-butylcatechol / ethanol / 120 h / Heating 2: KOH / Heating View Scheme

5-ethyl-2-methyl-pyridine (104-90-5) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium peroxo disulfate; ethanol / 220 °C 2: potassium hydroxide / 175 °C / Erhitzen unter vermindertem Druck View Scheme
Multi-step reaction with 2 steps 1: formic acid; water / 240 °C / 139011 Torr 2: potassium hydroxide / 175 °C / Erhitzen unter vermindertem Druck View Scheme
Multi-step reaction with 3 steps 1: water / 3 h / 150 - 160 °C / 3750.38 - 4500.45 Torr / Autoclave 2: triethylamine; p-toluenesulfonyl chloride / toluene / 0 - 5 °C 3: potassium carbonate / toluene / 10 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: water / 4 h / 155 °C / 4500.45 Torr / Autoclave 2: triethylamine; p-toluenesulfonyl chloride / toluene / 0 - 5 °C 3: potassium carbonate / toluene / 10 h / Reflux View Scheme

5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione hydrochloride (646519-89-3) → 5-ethyl-2-vinyl-pyridine (5408-74-2) + Pioglitazone (105355-27-9) + 5-(4-hydroxybenzyl)-2,4-thiazolidinedione (74772-78-4)

Conditions	Yield
With acetic acid; zinc In methanol Product distribution / selectivity; Industry scale;

2-hydroxymethyl-5-ethyl pyridine (768-61-6) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
With potassium hydroxide

5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione (646519-94-0) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / tetrahydrofuran / 12 h 2: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

2-(5-ethyl-1-oxypyridin-2-yl)ethanol (90643-32-6) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 8 steps 1: 0.5 h / 120 °C 2: sodium hydroxide / water / 2 h / 40 °C 3: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 4: N,N-dimethyl-formamide / 14 h / 80 °C 5: thionyl chloride / chloroform / 1 h / Reflux 6: acetic acid; piperidine / toluene / Heating 7: hydrogen / tetrahydrofuran / 12 h 8: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 8 steps 1: 0.5 h / 120 °C 2: sodium hydroxide / water / 2 h / 40 °C 3: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 4: N,N-dimethyl-formamide / 14 h / 80 °C 5: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 6: thionyl chloride / chloroform / 3 h / Reflux 7: hydrogen / tetrahydrofuran / 12 h 8: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 8 steps 1: 0.5 h / 120 °C 2: sodium hydroxide / water / 2 h / 40 °C 3: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 4: N,N-dimethyl-formamide / 14 h / 80 °C 5: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 6: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 7: thionyl chloride / chloroform / 2 h / Reflux 8: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

1-(5-ethylpyridin-2-yl)ethan-1,2-diol → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 2: N,N-dimethyl-formamide / 14 h / 80 °C 3: thionyl chloride / chloroform / 1 h / Reflux 4: acetic acid; piperidine / toluene / Heating 5: hydrogen / tetrahydrofuran / 12 h 6: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 6 steps 1: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 2: N,N-dimethyl-formamide / 14 h / 80 °C 3: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 4: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 5: thionyl chloride / chloroform / 2 h / Reflux 6: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 6 steps 1: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 2: N,N-dimethyl-formamide / 14 h / 80 °C 3: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 4: thionyl chloride / chloroform / 3 h / Reflux 5: hydrogen / tetrahydrofuran / 12 h 6: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

5-ethyl-2-[2-oxo-(1,3,2)dioxathiolan-4-yl]pyridine → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 14 h / 80 °C 2: thionyl chloride / chloroform / 1 h / Reflux 3: acetic acid; piperidine / toluene / Heating 4: hydrogen / tetrahydrofuran / 12 h 5: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 14 h / 80 °C 2: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 3: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 4: thionyl chloride / chloroform / 2 h / Reflux 5: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1: N,N-dimethyl-formamide / 14 h / 80 °C 2: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 3: thionyl chloride / chloroform / 3 h / Reflux 4: hydrogen / tetrahydrofuran / 12 h 5: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

4-[2-chloro-2-(5-ethyl-2-pyridyl)ethoxy]benzaldehyde → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; piperidine / toluene / Heating 2: hydrogen / tetrahydrofuran / 12 h 3: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde (471295-98-4) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: thionyl chloride / chloroform / 1 h / Reflux 2: acetic acid; piperidine / toluene / Heating 3: hydrogen / tetrahydrofuran / 12 h 4: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 4 steps 1: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 2: thionyl chloride / chloroform / 3 h / Reflux 3: hydrogen / tetrahydrofuran / 12 h 4: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 4 steps 1: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 2: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 3: thionyl chloride / chloroform / 2 h / Reflux 4: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

acetic acid 2-acetoxy-2-(5-ethyl-1-pyridin-2-yl)ethyl ester → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 7 steps 1: sodium hydroxide / water / 2 h / 40 °C 2: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 3: N,N-dimethyl-formamide / 14 h / 80 °C 4: thionyl chloride / chloroform / 1 h / Reflux 5: acetic acid; piperidine / toluene / Heating 6: hydrogen / tetrahydrofuran / 12 h 7: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 7 steps 1: sodium hydroxide / water / 2 h / 40 °C 2: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 3: N,N-dimethyl-formamide / 14 h / 80 °C 4: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 5: thionyl chloride / chloroform / 3 h / Reflux 6: hydrogen / tetrahydrofuran / 12 h 7: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 7 steps 1: sodium hydroxide / water / 2 h / 40 °C 2: thionyl chloride; triethylamine / dichloromethane / 1.25 h / 0 - 5 °C 3: N,N-dimethyl-formamide / 14 h / 80 °C 4: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 5: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 6: thionyl chloride / chloroform / 2 h / Reflux 7: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

5-{4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzylidene}-2,4-thiazolidene dione (646519-84-8) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / chloroform / 3 h / Reflux 2: hydrogen / tetrahydrofuran / 12 h 3: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 2: thionyl chloride / chloroform / 2 h / Reflux 3: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

2-bromo-1-(5-ethylpyridin-2-yl)ethanol (646519-81-5) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / tert-butyl alcohol / 1.17 h / Reflux 1.2: 11 h / Reflux 2.1: thionyl chloride / chloroform / 1 h / Reflux 3.1: acetic acid; piperidine / toluene / Heating 4.1: hydrogen / tetrahydrofuran / 12 h 5.1: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / tert-butyl alcohol / 1.17 h / Reflux 1.2: 11 h / Reflux 2.1: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 3.1: thionyl chloride / chloroform / 3 h / Reflux 4.1: hydrogen / tetrahydrofuran / 12 h 5.1: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / tert-butyl alcohol / 1.17 h / Reflux 1.2: 11 h / Reflux 2.1: pyrrolidine / methanol / 2 h / 50 - 55 °C / Large scale 3.1: sodium tetrahydroborate; butane-2,3-dione dioxime; cobalt(II) chloride hexahydrate / water; N,N-dimethyl-formamide / 4 h / 65 - 85 °C / Large scale 4.1: thionyl chloride / chloroform / 2 h / Reflux 5.1: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione (101931-00-4) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride / chloroform / 2 h / Reflux 2: zinc; acetic acid / 15 h / 25 - 30 °C View Scheme

toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester (144809-27-8) → 5-ethyl-2-vinyl-pyridine (5408-74-2)

Conditions	Yield
With potassium carbonate In toluene for 10h; Reflux;

5-ethyl-2-vinyl-pyridine (5408-74-2) + 4-aminotiophenol (1193-02-8) → 4-[2-(5-Ethyl-pyridin-2-yl)-ethylsulfanyl]-phenylamine (136401-93-9)

Conditions	Yield
Ambient temperature;	95%

5-ethyl-2-vinyl-pyridine (5408-74-2) → 2-bromo-1-(5-ethylpyridin-2-yl)ethanol (646519-81-5)

Conditions	Yield
With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 1.16667h; Reagent/catalyst; Solvent; Temperature; Time;	95%
With water; bromine; potassium bromide at 60 - 65℃; for 0.666667h; Product distribution / selectivity;	86%
With N-Bromosuccinimide; water In 1,4-dioxane at 25 - 30℃; for 4h; Product distribution / selectivity;	85%
With N-Bromosuccinimide; water In tetrahydrofuran at 25 - 30℃; for 4h; Product distribution / selectivity;	82%

5-ethyl-2-vinyl-pyridine (5408-74-2) → 1-(5-ethyl-2-pyridinyl)ethanone (286411-85-6) + 2-bromo-1-(5-ethylpyridin-2-yl)ethanol (646519-81-5) + 2-(1-bromovinyl)-5-ethylpyridine

Conditions	Yield
With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 1h; Product distribution / selectivity;	A n/a B 93% C n/a
With N-Bromosuccinimide; water In dimethyl sulfoxide at -5 - 0℃; for 0.5h; Product distribution / selectivity;	A 5% B 88% C 6%

5-ethyl-2-vinyl-pyridine (5408-74-2) → 5-ethyl-2-oxiran-2-ylpyridine

Conditions	Yield
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 1.5h; Stage #2: With sodium hydroxide In water; tert-butyl alcohol for 0.75h; Product distribution / selectivity;	92%
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In dimethyl sulfoxide at -5 - 0℃; for 1h; Stage #2: With potassium carbonate In methanol; water; dimethyl sulfoxide at 25 - 30℃; for 1h; Product distribution / selectivity;	80%
With N-Bromosuccinimide; acetic acid In water; tert-butyl alcohol at 10℃; for 1h; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;
Multi-step reaction with 2 steps 1: water; N-Bromosuccinimide / tert-butyl alcohol / 1.17 h / 25 - 30 °C 2: potassium carbonate / tert-butyl alcohol; water / 1 h / 25 - 30 °C View Scheme
Multi-step reaction with 2 steps 1: water; N-Bromosuccinimide / dimethyl sulfoxide / 0.5 h / -5 - 0 °C 2: potassium carbonate / tert-butyl alcohol; water / 1 h / 25 - 30 °C View Scheme

5-ethyl-2-vinyl-pyridine (5408-74-2) + phenindione (83-12-5) → 2-phenyl-2-[-(5-ethyl-2-pyridyl)ethyl]indane-1,3-dione

Conditions	Yield
In ethanol for 40h; Heating;	90%

5-ethyl-2-vinyl-pyridine (5408-74-2) → 2-bromo-1-(5-ethylpyridin-2-yl)ethanol (646519-81-5) + 2-(1-bromovinyl)-5-ethylpyridine

Conditions	Yield
With N-Bromosuccinimide; water In dimethyl sulfoxide at -5 - 0℃; for 0.5h;	A 88% B 6%

5-ethyl-2-vinyl-pyridine (5408-74-2) + 4-hydroxy-benzaldehyde (123-08-0) → 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde (471295-98-4) + 4-[1-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde (471296-00-1)

Conditions	Yield
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 1.5h; Industry scale; Stage #2: With sodium hydroxide In water; tert-butyl alcohol for 0.75h; Industry scale; Stage #3: 4-hydroxy-benzaldehyde With PEG 4000; sodium hydroxide In water; toluene at 78℃; for 17h; Product distribution / selectivity;	A 84% B n/a
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In tert-butyl alcohol at 25℃; for 1.5h; Industry scale; Stage #2: With sodium hydroxide In water; tert-butyl alcohol for 0.75h; Stage #3: 4-hydroxy-benzaldehyde With sodium hydroxide In water; toluene at 78℃; for 17h; Product distribution / selectivity;	A 83% B n/a
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water; 18-crown-6 ether In tert-butyl alcohol at 25 - 30℃; for 1.5h; Stage #2: With sodium hydroxide In water; tert-butyl alcohol for 0.75h; Stage #3: 4-hydroxy-benzaldehyde With sodium hydroxide; 18-crown-6 ether In water; toluene at 78℃; for 24h; Product distribution / selectivity;	A 81% B n/a
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 2.5h; Stage #2: 4-hydroxy-benzaldehyde With potassium carbonate In tert-butyl alcohol at 75 - 80℃; for 18h; Product distribution / selectivity;	A 79% B n/a

5-ethyl-2-vinyl-pyridine (5408-74-2) + 4-hydroxy-benzaldehyde (123-08-0) → 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde (471295-98-4)

Conditions	Yield
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide In water; tert-butyl alcohol at 25℃; for 1.5h; Large scale; Stage #2: With sodium hydroxide In water; tert-butyl alcohol for 0.75h; Large scale; Stage #3: 4-hydroxy-benzaldehyde With sodium hydroxide In water; toluene at 78℃; for 17h; Reagent/catalyst; Solvent; Temperature; Time; Large scale;	84%

5-ethyl-2-vinyl-pyridine (5408-74-2) + 4-hydroxybenzaldehyde potassium salt (58765-11-0) → 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde (471295-98-4)

Conditions	Yield
Stage #1: 5-ethyl-2-vinyl-pyridine With N-Bromosuccinimide; water In tert-butyl alcohol at 25 - 30℃; for 2.5h; Stage #2: 4-hydroxybenzaldehyde potassium salt In tert-butyl alcohol at 75 - 80℃; for 18h;	79%

5-ethyl-2-vinyl-pyridine (5408-74-2) + 1-(2-Methoxyphenyl)piperazine (35386-24-4) + (2E)-but-2-enedioic acid (110-17-8) → 1-(2-methoxyphenyl)-4-<2-<2-(5-ethyl)pyridyl>ethyl>piperazine fumarate (90126-10-6)

Conditions	Yield
With acetic acid 1.) ethanol, 5 h, reflux; 2.) acetone;	64%

5-ethyl-2-vinyl-pyridine (5408-74-2) + [(hydridotris(pyrazolyl)borato)RuCl2(NO)] (137729-45-4) → (BH(C3H3N2)3)RuCl(NOC2H2NC5H3C2H5)

Conditions	Yield
With triethylamine In dichloromethane treatment of Ru-complex with 2-vinylpyridine in the presence of excess of triethylamine in refluxing CH2Cl2;	56%

5-ethyl-2-vinyl-pyridine (5408-74-2) → 2-bromo[5-ethylpyridin-2-yl]ethyl bromide

Conditions	Yield
With bromine In tetrachloromethane for 2h; Product distribution / selectivity;	43%
With bromine In tetrachloromethane at 0 - 5℃; for 2h;

5-ethyl-2-vinyl-pyridine (5408-74-2) → 3-Ethyl-5-(5-ethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-quinoline (76162-64-6)

Conditions	Yield
With PPA In phosphoric acid at 180 - 200℃; for 8h;	42%

5-ethyl-2-vinyl-pyridine (5408-74-2) + N-phenyl-maleimide (941-69-5) → 5-(2,5-Dioxo-1-phenyl-pyrrolidin-3-yl)-8-ethyl-2-phenyl-3a,4,5,9b-tetrahydro-pyrrolo[3,4-f]quinoline-1,3-dione

Conditions	Yield
In acetic anhydride for 15h; Heating;	30%

5-ethyl-2-vinyl-pyridine (5408-74-2) + 1,3-di(aminomethyl)benzene (1477-55-0) → [3-({Bis-[2-(5-ethyl-pyridin-2-yl)-ethyl]-amino}-methyl)-benzyl]-bis-[2-(5-ethyl-pyridin-2-yl)-ethyl]-amine (147151-69-7)

Conditions	Yield
With acetic acid In methanol for 168h; Heating;	18%

5-ethyl-2-vinyl-pyridine (5408-74-2) + carbonylchlorohydridotris(triphenylphosphine)ruthenium(II) (157072-60-1, 166941-05-5, 16971-33-8, 61521-25-3) → Ru(CH2CH2(C2H5C5H3N))Cl(CO)(P(C6H5)3)2

Conditions	Yield
In tetrahydrofuran under N2, a THF suspn. of 1 equiv of Ru-complex and 1.5 equiv of 5-ethyl-2-vinylpyridine was stirred at room temp. for 10 h; elem. anal.;	17%

5-ethyl-2-vinyl-pyridine (5408-74-2) → bis<2-(2-(5-ethylpyridyl)ethyl)>amine (154743-00-7)

Conditions	Yield
With ammonium chloride In methanol for 48h; Heating;	16.5%

pyrrolidine (123-75-1) + 5-ethyl-2-vinyl-pyridine (5408-74-2) → 5-ethyl-2-(2-pyrrolidino-ethyl)-pyridine (91904-22-2)

Conditions	Yield
With acetic acid

piperidine (110-89-4) + 5-ethyl-2-vinyl-pyridine (5408-74-2) → 5-ethyl-2-(2-piperidino-ethyl)-pyridine (43058-52-2)

Conditions	Yield
With acetic acid

morpholine (110-91-8) + 5-ethyl-2-vinyl-pyridine (5408-74-2) → 4-[2-(5-ethyl-pyridin-2-yl)-ethyl]-morpholine (91904-47-1)

Conditions	Yield
With acetic acid

Thiophene-2-thiol (7774-74-5) + 5-ethyl-2-vinyl-pyridine (5408-74-2) → 5-ethyl-2-(2-[2]thienylmercapto-ethyl)-pyridine (100373-67-9)

5-ethyl-2-vinyl-pyridine (5408-74-2) + isoquinoline (119-65-3) + isoquinoline hydrochloride (21364-46-5) → 2-[2-(5-ethyl-[2]pyridyl)-ethyl]-isoquinolinium; chloride

Conditions	Yield
at 140℃;

5-ethyl-2-vinyl-pyridine (5408-74-2) + indole (120-72-9) → 3-[2-(5-ethyl-pyridin-2-yl)-ethyl]-indole (16571-55-4)

Conditions	Yield
With acetic acid

5-ethyl-2-vinyl-pyridine (5408-74-2) + Succinimide (123-56-8) → N-[2-(5-ethyl-[2]pyridyl)-ethyl]-succinimide (97030-49-4)

5-ethyl-2-vinyl-pyridine (5408-74-2) + methanol (67-56-1) → 5-ethyl-2-(2-methoxy-ethyl)-pyridine

Conditions	Yield
With potassium hydroxide at 150℃; unter Druck;

5-ethyl-2-vinyl-pyridine (5408-74-2) + 1-methylindole (603-76-9) → 3-[2-(5-ethyl-pyridin-2-yl)-ethyl]-1-methyl-indole (16568-58-4)

Conditions	Yield
With acetic acid

5-ethyl-2-vinyl-pyridine (5408-74-2) + phthalimide (136918-14-4) → N-[2-(5-ethyl-pyridin-2-yl)-ethyl]-phthalimide (17624-24-7)

Conditions	Yield
With acetic acid at 140℃;

5-ethyl-2-vinyl-pyridine (5408-74-2) + 4-methyl pentanamine (5344-20-7) → [2-(5-ethyl-[2]pyridyl)-ethyl]-isohexyl-amine (131241-20-8)

Conditions	Yield
With acetic acid

5-ethyl-2-vinyl-pyridine (5408-74-2) + thioacetic acid (507-09-5) → thioacetic acid S-[2-(5-ethyl-[2]pyridyl)-ethyl ester]

Conditions	Yield
anfangs bei -40grad;

Upstream product

• 104-90-5 5-ethyl-2-methyl-pyridine 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 646519-81-5 2-bromo-1-(5-ethylpyridin-2-yl)ethanol 
• 646519-84-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzylidene}-2,4-thiazolidene dione 
• 471295-98-4 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde 
• 646519-82-6 5-ethyl-2-[2-oxo-(1,3,2)dioxathiolan-4-yl]pyridine 
• 90643-32-6 2-(5-ethyl-1-oxypyridin-2-yl)ethanol 
• 646519-94-0 5-{4-[2-chloro-2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 768-61-6 2-hydroxymethyl-5-ethyl pyridine 
• 646519-89-3 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione hydrochloride 
• 646519-88-2 5-{4-[2-chloro-2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-2,4-thiazolidene dione 
• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 43058-52-2 5-Ethyl-2-<2-piperidino-ethyl>-pyridin 
• 17624-24-7 N-<2-(5-Ethyl-2-pyridyl)ethyl>-phthalimid 
• 119531-91-8 N-[2-(5-ethyl-[2]pyridyl)-ethyl]-N-benzyl-aniline 
• 101586-32-7 N-[2-(5-ethyl-[2]pyridyl)-ethyl]-o-anisidine 
• 51770-56-0 [2-(5-ethyl-[2]pyridyl)-ethyl]-benzyl-amine 
• 102895-64-7 bis-[2-(5-ethyl-[2]pyridyl)-ethyl]-benzyl-amine 
• 100957-31-1 N-[2-(5-ethyl-[2]pyridyl)-ethyl]-aniline 
• 471295-98-4 4-[2-(5-ethylpyridin-2-yl)-2-hydroxyethoxy]benzaldehyde 
• 471296-00-1 4-[1-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde 
• 101931-00-4 5-{4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxyethoxy]benzyl}-2,4-thiazolidinedione 
• 146062-49-9 rac-5-({p-[2-(5-ethylpyridin-2-yl)-2-oxoethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione 
• 105355-27-9 Pioglitazone 
• 646519-90-6 5-{4-[2-(5-ethylpyridin-2-yl)-2-mesylethoxy]benzylidene}-2,4-thiazolidene dione 
• 646519-92-8 5-{4-[2-(5-ethylpyridin-2-yl)-2-tosylethoxy]benzylidene}-2,4-thiazolidene dione 

Relevant articles and documents

Development of an improved and scalable process for 2-(5-ethylpyridin-2-yl) ethan-1-ol: Solvent-free reaction and recycling of the starting material 5-ethyl-2-picoline

The main objective of this exercise was to develop a more efficient process for 2-(5-ethylpyridin-2-yl)ethan-1-ol (1), which is the key intermediate in the synthesis of pioglitazone hydrochloride. This process not only features the yield improvement of (1) by optimizing reaction variables in solvent-free conditions but also highlights improving the mass efficiency of 5-ethyl-2-picoline (2), thereby reducing the effluent load per kilogram of the intermediate.

A NOVEL PROCESS TO PREPARE PIOGLITAZONE VIA SEVERAL NOVEL INTERMEDIATES.

A novel process for preparing thiazolidinediones, preferably Pioglitazone, are described. Also described are novel intermediates involved in its synthesis and process for their preparation and use in medicine.

Production of benzaldehyde compounds

A method of producing a compound represented by the formula: STR1 wherein R1 stands for hydrogen or an optionally substituted alkyl or acyl group, which comprises reacting a compound represented by the formula: STR2 wherein R1 is of the same meaning as defined above, and R2 stands for an optionally halolgenated alkyl group or an optionally substituted phenyl group with a compound represented by the formula: STR3 in a lower alcohol in the presence of an alkali metal or alkaline earth metal carbonate; the compound (III) being useful as starting compounds for producing thiazolidinedione derivatives having hypoglycemic and hypolipidemic activities.