(R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one

Base Information

• Chemical Name: (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one
• CAS No.: 309243-64-9
• Molecular Formula: C₁₃H₂₄O₂Si
• Molecular Weight: 240.418
• Mol file: 309243-64-9.mol

Synonyms:(R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one

Chemical Property of (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one

There total 12 articles about (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-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: 92.0%

(R)-4-hydroxy-3-methyl-cyclohex-2-en-1-one (184653-97-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one (309243-64-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(00)00645-1

Reference yield: 90.0%

methylmagnesium bromide (75-16-1) + <(4R)-(+)-tert-Butoxydimethylsiloxy>-2-cyclohexen-1-on (164577-42-8) → (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one (309243-64-9)

Guidance literature:

methylmagnesium bromide; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 0.666667h;

<(4R)-(+)-tert-Butoxydimethylsiloxy>-2-cyclohexen-1-on; With chloro-trimethyl-silane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - 25 ℃;

With oxygen; palladium diacetate; In dimethyl sulfoxide; at 25 ℃; for 18h; under 760.051 Torr; Further stages.;

DOI:10.1021/ja074297d

Reference yield: 70.0%

C13H26O2Si → (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one (309243-64-9)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; optical yield given as %ee; Molecular sieve;

DOI:10.1021/ol2010819

upstream raw materials:

(R)-4-hydroxy-3-methyl-cyclohex-2-en-1-one

tert-butyldimethylsilyl chloride

methylmagnesium bromide

<(4R)-(+)-tert-Butoxydimethylsiloxy>-2-cyclohexen-1-on

Downstream raw materials:

methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate

(1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol

C₁₃H₂₃BrO₂Si

C₁₅H₂₆O₃Si