(R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester
• CAS No.: 197845-70-8
• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.246
• Mol file: 197845-70-8.mol

Synonyms:(R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester

Chemical Property of (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester

There total 3 articles about (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester 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: 80.0%

(+)-methyl (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate (197972-03-5) → (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester (197845-70-8)

Guidance literature:

With boron trifluoride diethyl etherate; pyridinium chlorochromate; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1016/S0040-4039(97)01793-0

Reference yield:

methyl (Z)-7-methyl-3-((trimethylsilyl)methyl)octa-2,6-dienoate (81752-85-4) → (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester (197845-70-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / AD mix-β, aq. t-BuOH, MeSO2NH2 / 26 h / 0 °C

2: 80 percent / 1.) MsCl, Et₃N; 2.) DBU / 1.) -40 deg C to -20 deg C, 1 h; 2.) 0 deg C

3: 80 percent / BF₃*OEt, PCC / CH₂Cl₂ / 10 h / Ambient temperature

With methanesulfonamide; boron trifluoride diethyl etherate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; pyridinium chlorochromate; tert-butyl alcohol; In dichloromethane;

DOI:10.1016/S0040-4039(97)01793-0

Reference yield:

(-)-methyl (6R)-(Z)-6,7-dihydroxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate (197845-69-5) → (R)-2,2-Dimethyl-6-methylene-3-oxo-cyclohexanecarboxylic acid methyl ester (197845-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 1.) MsCl, Et₃N; 2.) DBU / 1.) -40 deg C to -20 deg C, 1 h; 2.) 0 deg C

2: 80 percent / BF₃*OEt, PCC / CH₂Cl₂ / 10 h / Ambient temperature

With boron trifluoride diethyl etherate; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4039(97)01793-0

upstream raw materials:

(+)-methyl (6S)-(Z)-6,7-epoxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate

methyl (Z)-7-methyl-3-((trimethylsilyl)methyl)octa-2,6-dienoate

(-)-methyl (6R)-(Z)-6,7-dihydroxy-7-methyl-3-(trimethylsilyl)methyl-2-octenoate