2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde

Base Information

• Chemical Name: 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde
• CAS No.: 603129-12-0
• Molecular Formula: C₁₈H₃₄O₂Si
• Molecular Weight: 310.552
• Mol file: 603129-12-0.mol

Synonyms:2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde

Chemical Property of 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde

There total 2 articles about 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde 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: 90.0%

2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]ethanol (603129-11-9) → 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde (603129-12-0)

Guidance literature:

With silica gel; pyridinium chlorochromate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(02)02733-8

Reference yield:

methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate (302840-48-8) → 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde (603129-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / LAH / diethyl ether / 2 h / 0 - 20 °C

2: 90 percent / PCC; silica gel / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; silica gel; pyridinium chlorochromate; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(02)02733-8

Reference yield: 92.0%

diazoacetic acid ethyl ester (623-73-4) + 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetaldehyde (603129-12-0) → ethyl 4-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]-3-oxobutanoate (603129-09-5)

Guidance literature:

tin(ll) chloride; In dichloromethane; at 20 ℃; for 6h;

DOI:10.1016/S0040-4039(02)02733-8

upstream raw materials:

2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]ethanol

methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

Downstream raw materials:

ethyl 4-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]-3-oxobutanoate

ethyl 2-diazo-4-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]-3-oxobutanoate