methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate

Base Information

• Chemical Name: methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate
• CAS No.: 146983-20-2
• Molecular Formula: C₂₂H₂₈O₃Si
• Molecular Weight: 368.548
• Mol file: 146983-20-2.mol

Synonyms:methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate

Chemical Property of methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate

There total 3 articles about methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate 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: 98.0%

methyl (2E)-2-(hydroxymethyl)-2-butenoate (28127-64-2) + tert-butylchlorodiphenylsilane (58479-61-1) → methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate (146983-20-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃;

DOI:10.1016/S0040-4039(00)70684-8

Reference yield:

methyl 2-(bromomethyl)-2-butenoate (33935-64-7) → methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate (146983-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / NaOAc / methanol / 3.5 h / Heating

2: imidazole / dimethylformamide / 10 h / 20 °C

With 1H-imidazole; sodium acetate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02773-9

Reference yield:

methyl 3-hydroxy-2-methylenebutyrate (98837-36-6,111002-28-9,112572-93-7,18020-65-0) → methyl (2E)-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-butenoate (146983-20-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / NBS, DMS / CH₂Cl₂ / 16 h / 25 °C

2: 1.) NaOAc, 2.) K₂CO₃ / 1.) MeOH, refluxed, 3 h, 2.) 25 deg C, 15 h

3: imidazole / dimethylformamide / 16 h / 25 °C

With 1H-imidazole; N-Bromosuccinimide; 2,3-dimercapto-succinic acid; sodium acetate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00060a035

upstream raw materials:

methyl (2E)-2-(hydroxymethyl)-2-butenoate

tert-butylchlorodiphenylsilane

methyl 2-(bromomethyl)-2-butenoate

methyl 3-hydroxy-2-methylenebutyrate

Downstream raw materials:

(S,E)-tert-butyl((2-ethyl-4-iodobut-3-en-1-yl)oxy)diphenylsilane

(S)-methyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)butanoate

(R)-methyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)butanoate

(R)-2-(((tert-butyldiphenylsilyl)oxy)methyl)butanal