trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol

Base Information

• Chemical Name: trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol
• CAS No.: 31930-44-6
• Molecular Formula: C₁₂H₁₈OSi
• Molecular Weight: 206.36
• Mol file: 31930-44-6.mol

Synonyms:

Chemical Property of trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol

There total 13 articles about trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol 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: 99.0%

1-phenyl-3-trimethylsilylprop-2-yn-1-ol (89530-34-7) → trans-1-phenyl-3-trimethylsilyl-2-propen-1-ol (31930-44-6,82476-31-1,119046-48-9,119180-85-7,84840-97-1)

Guidance literature:

1-phenyl-3-trimethylsilylprop-2-yn-1-ol; With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 - 20 ℃; for 12h; Inert atmosphere;

With hydrogenchloride; water; In diethyl ether; toluene; at 0 ℃; Inert atmosphere;

DOI:10.1002/anie.200904402

Reference yield: 76.0%

1-phenyl-3-trimethylsilylprop-2-yn-1-ol (89530-34-7) → 1-phenyl-3-(trimethylsilyl)prop-2-en-1-ol (31930-44-6,84840-97-1,119046-48-9,119180-85-7,82476-31-1)

Guidance literature:

With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201800483

Reference yield:

1-Phenyl-2-propyn-1-ol (4187-87-5) → 1-phenyl-3-(trimethylsilyl)prop-2-en-1-ol (31930-44-6,84840-97-1,119046-48-9,119180-85-7,82476-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / -78 - 22 °C

1.2: tetrahydrofuran; hexane / -78 - 22 °C

2.1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene; diethyl ether / 0 - 22 °C

With n-butyllithium; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; toluene;

DOI:10.1021/ol071331k

upstream raw materials:

1-phenyl-3-trimethylsilylprop-2-yn-1-ol

1-Phenyl-2-propyn-1-ol

benzaldehyde

bis(pinacol)diborane

Downstream raw materials:

(E)-1-phenyl-3-(trimethylsilyl)prop-2-en-1-one

1-phenyl-3-trimethylsilanylpropen-1-one

1,4-Diphenylprop-3-en-1-one

(E)-3-ethoxy-3-phenyl-1-(trimethylsilyl)-1-propene

Refernces

• 1、 Zhang, Yuxia,Huang, Jie,Guo, Yingying,Li, Lin,Fu, Zhenqian,Huang, Wei. "Access to Enantioenriched Organosilanes from Enals and β-Silyl Enones: Carbene Organocatalysis". supporting information. p. 4594 - 4598. Retrieved 2018/03/21.
• 2、 Gan, Zubao,Wu, Ya,Gao, Lu,Sun, Xianwei,Lei, Jian,Song, Zhenlei,Li, Linjie. "Studies on retro-[1,4] Brook rearrangement of 3-silyl allyloxysilanes. Observation of the formation of unusual 3,3-bissilyl enols". supporting information; experimental part. p. 6928 - 6934. Retrieved 2012/08/29.