1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol

Base Information

• Chemical Name: 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol
• CAS No.: 1374575-83-3
• Molecular Formula: C₁₂H₁₆O₂Si
• Molecular Weight: 220.343
• Mol file: 1374575-83-3.mol

Synonyms:1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol

Chemical Property of 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol

There total 6 articles about 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol 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: 78.0%

salicylaldehyde (90-02-8) + trimethylsilylacetylene (1066-54-2) → 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol (1374575-83-3)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at -78 - -40 ℃; for 4h;

salicylaldehyde; In tetrahydrofuran; at -78 ℃; for 12h;

DOI:10.1021/ol503662g

Reference yield: 69.0%

2-diethyl(trimethylsilylethynyl)silylbenzaldehyde → 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol (1374575-83-3)

Guidance literature:

With dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; water; at 20 ℃; for 7h; Inert atmosphere;

DOI:10.1021/ja510089c

Reference yield:

2-diethyl(trimethylsilylethynyl)silylbenzaldehyde → 1-(o-hydroxyphenyl)-3-trimethylsilylpropargylic alcohol (1374575-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere

2: potassium hydrogencarbonate; dihydrogen peroxide / tetrahydrofuran; methanol; water / 7 h / 20 °C / Inert atmosphere

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; dihydrogen peroxide; potassium hydrogencarbonate; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja510089c

upstream raw materials:

salicylaldehyde

trimethylsilylacetylene

2-bromobenzaldehyde diethyl acetal

Downstream raw materials:

2-benzyloxymethyl-1-benzofuran

C₁₅H₁₈O₂

2-(1-methoxyprop-2-ynyl)phenol

1-(o-hydroxyphenyl)propargylic alcohol

Refernces

• 1、 Zhang, Ming,Yang, Jianlin,Xu, Qing,Dong, Chao,Han, Li-Biao,Shen, Ruwei. "Copper-Catalyzed Dehydrative Cyclization of 1-(2-Hydroxyphenyl)propargyl Alcohols with P(O)H Compounds for the Synthesis of 2-Phosphorylmethylbenzofurans". supporting information. p. 334 - 345. Retrieved 2018/01/15.
• 2、 Hoshimoto, Yoichi,Yabuki, Hayato,Kumar, Ravindra,Suzuki, Haruka,Ohashi, Masato,Ogoshi, Sensuke. "Highly efficient activation of organosilanes with η2-aldehyde nickel complexes: Key for catalytic syntheses of aryl-, vinyl-, and alkynyl-benzoxasiloles". . p. 16752 - 16755. Retrieved 2015/01/16.