6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

Base Information

• Chemical Name: 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde
• CAS No.: 89656-03-1
• Molecular Formula: C₂₁H₂₆OS
• Molecular Weight: 326.503
• Mol file: 89656-03-1.mol

Synonyms:6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

Chemical Property of 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

There total 21 articles about 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde 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:

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde (89656-03-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 99.1 percent / p-toluenesulfonic acid / acetic acid / 5 h / Ambient temperature

2: p-toluenesulfonic acid / benzene / 15 h / Heating

3: 73.8 percent / Na, liquid NH₃ / diethyl ether; 1,2-dimethoxy-ethane / 1 h

4: 1.) BH₃*THF, 2.) 3 N NaOH, 30percent H₂₀₂ / 1.) THF, a) 0 deg C, 3 h, b) RT, overnight, 2.) THF, 4 h

5: 89.2 percent / NaH / benzene / Ambient temperature

6: K₂CO₃ / acetone / 20 h / Heating

7: NaOEt / ethanol / 7 h / Heating

8: dimethylsulfoxide / 15 h / 55 - 60 °C

9: 85 percent / 1 N HCl / tetrahydrofuran; acetic acid / Ambient temperature

10: 1.) NaH, 2.) EtOH / 1.) 0 deg C, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, overnight

11: 1.) pyridine, p-toluenesulfonyl chloride / 1.) 1 h, 0 deg C, 2.) a) 0 deg C, 1 h, b) 5 deg C, overnight

With pyridine; hydrogenchloride; sodium hydroxide; borane-THF; ethanol; ammonia; dihydrogen peroxide; sodium ethanolate; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;

DOI:10.1021/jo00356a002

Reference yield:

5,5-(ethylenedioxy)-4aβ-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene (90878-77-6) → 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde (89656-03-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) BH₃*THF, 2.) 3 N NaOH, 30percent H₂₀₂ / 1.) THF, a) 0 deg C, 3 h, b) RT, overnight, 2.) THF, 4 h

2: 89.2 percent / NaH / benzene / Ambient temperature

3: K₂CO₃ / acetone / 20 h / Heating

4: NaOEt / ethanol / 7 h / Heating

5: dimethylsulfoxide / 15 h / 55 - 60 °C

6: 85 percent / 1 N HCl / tetrahydrofuran; acetic acid / Ambient temperature

7: 1.) NaH, 2.) EtOH / 1.) 0 deg C, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, overnight

8: 1.) pyridine, p-toluenesulfonyl chloride / 1.) 1 h, 0 deg C, 2.) a) 0 deg C, 1 h, b) 5 deg C, overnight

With pyridine; hydrogenchloride; sodium hydroxide; borane-THF; ethanol; dihydrogen peroxide; sodium ethanolate; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; In tetrahydrofuran; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;

DOI:10.1021/jo00356a002

Reference yield:

5,5-(ethylenedioxy)-4aβ-methylperhydronaphthalen-1-one (90878-79-8,90878-80-1,100432-16-4,100432-17-5) → 6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde (89656-03-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 89.2 percent / NaH / benzene / Ambient temperature

2: K₂CO₃ / acetone / 20 h / Heating

3: NaOEt / ethanol / 7 h / Heating

4: dimethylsulfoxide / 15 h / 55 - 60 °C

5: 85 percent / 1 N HCl / tetrahydrofuran; acetic acid / Ambient temperature

6: 1.) NaH, 2.) EtOH / 1.) 0 deg C, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, overnight

7: 1.) pyridine, p-toluenesulfonyl chloride / 1.) 1 h, 0 deg C, 2.) a) 0 deg C, 1 h, b) 5 deg C, overnight

With pyridine; hydrogenchloride; ethanol; sodium ethanolate; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; In tetrahydrofuran; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;

DOI:10.1021/jo00356a002

upstream raw materials:

methyl-phenyl-thioether

2-<(butylthio)methylene>-6β,8aβ-dimethyl-5-methylene-trans-perhydronaphthalen-1-one

(4aS,6S,8aS)-2-[1-Butylsulfanyl-meth-(E)-ylidene]-6,8a-dimethyl-5-methylene-octahydro-naphthalen-1-one

(phenylthio)methyllithium

Downstream raw materials:

(+/-)-colorata-4(13)8-dienolide

7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan

6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde