methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate

Base Information

• Chemical Name: methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate
• CAS No.: 1383717-87-0
• Molecular Formula: C₁₇H₂₄O₃Si
• Molecular Weight: 304.461
• Mol file: 1383717-87-0.mol

Synonyms:methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate

Chemical Property of methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate

There total 5 articles about methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate 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: 83.0%

propynoic acid methyl ester (922-67-8) + 4-(tert-butyldimethylsiloxymethyl)iodobenzene (147283-96-3) → methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate (1383717-87-0)

Guidance literature:

propynoic acid methyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

4-(tert-butyldimethylsiloxymethyl)iodobenzene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; zinc dibromide; In tetrahydrofuran; hexane; at -78 - 35 ℃; for 16h;

DOI:10.1016/j.bmcl.2012.05.012

Reference yield: 76.0%

tert-butyl[(4-ethynylphenyl)methoxy]dimethylsilane (1093190-17-0) + methyl chloroformate (79-22-1) → methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate (1383717-87-0)

Guidance literature:

tert-butyl[(4-ethynylphenyl)methoxy]dimethylsilane; With lithium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 - -40 ℃; for 1h;

methyl chloroformate; In tetrahydrofuran; toluene; at -40 - 20 ℃;

Reference yield:

4-iodobenzoic acid (619-58-9) → methyl 3-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-prop-2-ynoate (1383717-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: borane-THF / tetrahydrofuran / 14 h / -20 - 50 °C / Reflux

2.1: 1H-imidazole / N,N-dimethyl-formamide / 1.75 h / 20 °C

3.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 16 h / -78 - 35 °C

With 1H-imidazole; n-butyllithium; borane-THF; diisopropylamine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 3.2: Negishi coupling reaction;

DOI:10.1016/j.bmcl.2012.05.012

upstream raw materials:

tert-butyl[(4-ethynylphenyl)methoxy]dimethylsilane

methyl chloroformate

4-iodobenzoic acid

propynoic acid methyl ester

Downstream raw materials:

methyl 5-(4-((tert-butyldimethylsilyloxy)methyl)phenyl)-3-methylisoxazole-4-carboxylate

(+/-)-Ki16425

methyl 5-(4-(hydroxymethyl)phenyl)-3-methylisoxazole-4-carboxylate

methyl 5-(4-(chloromethyl)phenyl)-3-methylisoxazole-4-carboxylate