trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate

Base Information

• Chemical Name: trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate
• CAS No.: 211995-89-0
• Molecular Formula: C₁₈H₃₄O₂Si
• Molecular Weight: 310.552
• Mol file: 211995-89-0.mol

Synonyms:trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate

Chemical Property of trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate

There total 3 articles about trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate 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:

diethyl cyclohexane-trans-1,4-dicarboxylate (19145-96-1) → trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate (211995-89-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / LiAlH₄ / diethyl ether / 20 °C

2: 61 percent / pyridine / 2 h / 0 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4: 388.9 mg / tetrahydrofuran; hexane / 16 h / -60 - 20 °C

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1: Reduction / 2: Esterification / 3: Swern oxidation / 4: Wittig reaction;

DOI:10.1246/bcsj.71.1639

Reference yield:

trans-4-(pivaloyloxymethyl)cyclohexanemethanol → trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate (211995-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

2: 388.9 mg / tetrahydrofuran; hexane / 16 h / -60 - 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1: Swern oxidation / 2: Wittig reaction;

DOI:10.1246/bcsj.71.1639

Reference yield:

(2-trimethylsilylethylidene)triphenylphosphorane (63922-69-0) + trans-4-(pivaloyloxymethyl)cyclohexanecarbaldehyde (211995-87-8) → trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexylmethyl pivaloate (211995-89-0)

Guidance literature:

In tetrahydrofuran; hexane; at -60 - 20 ℃; for 16h;

DOI:10.1246/bcsj.71.1639

upstream raw materials:

(2-trimethylsilylethylidene)triphenylphosphorane

trans-4-(pivaloyloxymethyl)cyclohexanecarbaldehyde

diethyl cyclohexane-trans-1,4-dicarboxylate

Downstream raw materials:

trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanecarbaldehyde

trans-4-[(Z)-3-(trimethylsilyl)prop-1-en-1-yl]cyclohexanemethanol

Refernces