(E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone

Base Information

• Chemical Name: (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone
• CAS No.: 181648-56-6
• Molecular Formula: C₁₉H₂₆ClNO₃
• Molecular Weight: 351.873
• Mol file: 181648-56-6.mol

Synonyms:

Chemical Property of (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone

There total 14 articles about (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 65.0%

ethanol (64-17-5) + (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-2,5-pyrrolidinedione (181648-55-5) → (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone (181648-56-6)

Guidance literature:

With sodium tetrahydroborate; chloro-trimethyl-silane; for 1.25h;

DOI:10.1021/jo960673t

Reference yield:

4-Chloro-3-methylphenol (59-50-7) → (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone (181648-56-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / imidazole / dimethylformamide

2: 66 percent / NBS, benzoyl peroxide / CCl₄ / 2 h / Heating

3: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -35 deg C, 3 h

4: 94 percent / LiAlH₄ / diethyl ether / 1.5 h

5: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

6: 95 percent / tetrahydrofuran / 2 h

7: 96 percent / propionic acid / 1.) reflux, 1 h, 2.) 160 deg C, 1 h

8: 1.) KOH, 2.) imidazole / 1.) MeOH, H₂O, room temperature, 4 h, 2.) DMF, 25 deg C, overnight

9: 1.) Et₃N, (PhO)2P(O)N₃ / 1.) dioxane, room temperature, 30 min; reflux, 40 min, 2.) reflux, overnight

10: 63 percent / KF / dimethylformamide / 27 h

11: 100 percent / KOH / ethanol; H₂O / 48 h / Heating

12: 65 percent / DCC / tetrahydrofuran

13: 70 percent / AcCl / 24 h / Heating

14: 65 percent / NaBH₄, Me₃SiCl / 1.25 h

With 1H-imidazole; potassium fluoride; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; Perbenzoic acid; oxalyl dichloride; diphenyl phosphoryl azide; dimethyl sulfoxide; propionic acid; triethylamine; acetyl chloride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo960673t

Reference yield:

tert-butyl-(4-chloro-3-methyl-phenoxy)-dimethyl-silane (181648-42-0) → (E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-5-ethoxy-2-pyrrolidinone (181648-56-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 66 percent / NBS, benzoyl peroxide / CCl₄ / 2 h / Heating

2: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -35 deg C, 3 h

3: 94 percent / LiAlH₄ / diethyl ether / 1.5 h

4: 100 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / -78 - 25 °C

5: 95 percent / tetrahydrofuran / 2 h

6: 96 percent / propionic acid / 1.) reflux, 1 h, 2.) 160 deg C, 1 h

7: 1.) KOH, 2.) imidazole / 1.) MeOH, H₂O, room temperature, 4 h, 2.) DMF, 25 deg C, overnight

8: 1.) Et₃N, (PhO)2P(O)N₃ / 1.) dioxane, room temperature, 30 min; reflux, 40 min, 2.) reflux, overnight

9: 63 percent / KF / dimethylformamide / 27 h

10: 100 percent / KOH / ethanol; H₂O / 48 h / Heating

11: 65 percent / DCC / tetrahydrofuran

12: 70 percent / AcCl / 24 h / Heating

13: 65 percent / NaBH₄, Me₃SiCl / 1.25 h

With 1H-imidazole; potassium fluoride; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; Perbenzoic acid; oxalyl dichloride; diphenyl phosphoryl azide; dimethyl sulfoxide; propionic acid; triethylamine; acetyl chloride; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo960673t

upstream raw materials:

ethanol

(E)-1-[6-(2-chloro-5-methoxyphenyl)-3-hexenyl]-2,5-pyrrolidinedione

4-Chloro-3-methylphenol

tert-butyl-(4-chloro-3-methyl-phenoxy)-dimethyl-silane

Refernces