3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

Base Information

• Chemical Name: 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester
• CAS No.: 116414-91-6
• Molecular Formula: C11H24O3Si
• Molecular Weight: 232.395
• Mol file: 116414-91-6.mol

Synonyms:

Chemical Property of 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

Chemical Property:

• PSA: 35.53000
• LogP: 2.95980

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

There total 4 articles about 3-(tert-Butyldimethylsiloxy)butyric 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: 95.4%

3-hydroxybutyric acid methyl ester (1487-49-6) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl-3-((tert-butyldimethylsilyl)oxy)butanoate (116414-91-6)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 30 ℃; for 3h; Inert atmosphere;

Reference yield:

tert-butyldimethylsilyl ether-β-hydroxybutyric acid ethyl ester (81327-43-7) → methyl-3-((tert-butyldimethylsilyl)oxy)butanoate (116414-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87.1 percent / aq. NaOH / methanol / 20 h

2: diethyl ether / 0.25 h

With sodium hydroxide; In methanol; diethyl ether;

DOI:10.1021/jo00385a024

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl-3-((tert-butyldimethylsilyl)oxy)butanoate (116414-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / imidazole / dimethylformamide / 8 h

2: 87.1 percent / aq. NaOH / methanol / 20 h

3: diethyl ether / 0.25 h

With 1H-imidazole; sodium hydroxide; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo00385a024

upstream raw materials:

diazomethane

tert-butyldimethylsilyl ether-β-hydroxybutyric acid

tert-butyldimethylsilyl ether-β-hydroxybutyric acid ethyl ester

tert-butyldimethylsilyl chloride

Downstream raw materials:

3-hydroxybutyric acid methyl ester

methyl 3-acetoxybutyrate

Refernces

• 1、 Ireland, Robert E.,Wardle, Robert B.. "3-Acyltetramic Acid Antibiotics. 3. An Approach to the Synthesis of Bu-2313". . p. 1780 - 1789. Retrieved 2007/10/02.