(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Base Information

• Chemical Name: (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one
• CAS No.: 182699-79-2
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22
• Mol file: 182699-79-2.mol

Synonyms:(+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Chemical Property of (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one

There total 6 articles about (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one 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: 99.0%

(3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one (477717-60-5) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Guidance literature:

With [NH₂Me₂][{RuCl((S)-segphos)}₂(μ-Cl)₃]; hydrogen; In 1,4-dioxane; at 40 ℃; for 6h; under 15001.5 Torr; diastereoselective reaction; Inert atmosphere; Autoclave;

DOI:10.1021/jacs.9b07297

Reference yield:

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanoic acid (287720-48-3) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Guidance literature:

With tert.-butylhydroperoxide; dipyridinium dichromate; Celite; In N,N-dimethyl-formamide; at 30 ℃; for 12h;

DOI:10.1002/hlca.19960790606

Reference yield:

2-(4-methyl-2-oxocyclohex-3-en-1-yl)acetic acid (20778-34-1) → (-)-(3aS,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-77-0) + (+)-(3aR,3aS,7aR)-3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (182699-79-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: formic acid; RuCl((R,R)-O-HT-TIPPsDPEN); 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 16 h / 60 - 80 °C / Inert atmosphere

2.1: sodium hydride; oxalic acid diethyl ester / tetrahydrofuran; mineral oil; ethanol / 4 h / 0 - 20 °C / Inert atmosphere

2.2: 0.25 h / 0 °C

3.1: [NH₂Me₂][{RuCl((S)-segphos)}₂(μ-Cl)₃]; hydrogen / 1,4-dioxane / 6 h / 40 °C / 15001.5 Torr / Inert atmosphere; Autoclave

With 1,4-diaza-bicyclo[2.2.2]octane; formic acid; RuCl((R,R)-O-HT-TIPPsDPEN); [NH₂Me₂][{RuCl((S)-segphos)}₂(μ-Cl)₃]; hydrogen; sodium hydride; oxalic acid diethyl ester; In tetrahydrofuran; 1,4-dioxane; ethanol; acetonitrile; mineral oil;

DOI:10.1021/jacs.9b07297

upstream raw materials:

(2RS)-2-<(1R)-4-methylcyclohex-3-enyl>propanoic acid

(3aS,7aS)-6-methyl-3-methylene-3a,4,5,7a-tetrahydrobenzofuran-2(3H)-one

2-(4-methyl-2-oxocyclohex-3-en-1-yl)acetic acid

3-Methylcyclohexanone