tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane
• CAS No.: 151950-98-0
• Molecular Formula: C₂₉H₃₄OSi
• Molecular Weight: 426.674
• Mol file: 151950-98-0.mol

Synonyms:tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane

There total 9 articles about tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane 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:

Trifluoro-methanesulfonic acid 2-[(Z)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-enyl]-phenyl ester (151950-87-7) → tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane (151950-98-0) + tert-Butyl-[(E)-2-((R)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane

Guidance literature:

With palladium diacetate; potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In tetrahydrofuran; at 50 ℃; for 336h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00071a079

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane (151950-98-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NEt₂, 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 3 h / 23 °C

2: 1.) Zn-Cu, Br₂CH₂CH₂Br, 2.) Pd(Ph)4 / 2.) THF, 70 deg C

3: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

4: Et₃N / CH₂Cl₂ / -78 - 0 °C

5: Pd(OAc)2, (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, K₂CO₃ / tetrahydrofuran / 336 h / 50 °C

With dmap; palladium diacetate; Br₂CH₂CH₂Br; Pd(Ph)4; tetrabutyl ammonium fluoride; copper; potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00071a079

Reference yield:

1-tert-butyldimethylsilyloxy-2-(2-propenyl)benzene (151950-94-6) → tert-Butyl-[(E)-2-((S)-1-methyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-vinyloxy]-diphenyl-silane (151950-98-0)

Guidance literature:

Multi-step reaction with 6 steps

1: BH₃*THF, aq. H₂O₂, NaOH / 0 °C

2: PH₃P, I₂, imidazole / benzene / 0 °C

3: 1.) Zn-Cu, Br₂CH₂CH₂Br, 2.) Pd(Ph)4 / 2.) THF, 70 deg C

4: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

5: Et₃N / CH₂Cl₂ / -78 - 0 °C

6: Pd(OAc)2, (R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, K₂CO₃ / tetrahydrofuran / 336 h / 50 °C

With 1H-imidazole; palladium diacetate; sodium hydroxide; borane-THF; Br₂CH₂CH₂Br; Pd(Ph)4; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; copper; potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triethylamine; triphenylphosphine; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja00071a079

upstream raw materials:

Trifluoro-methanesulfonic acid 2-[(Z)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-hex-4-enyl]-phenyl ester

tert-butylchlorodiphenylsilane

1-tert-butyldimethylsilyloxy-2-(2-propenyl)benzene

3-(2-((tert-butyldimethylsilyl)oxy)phenyl)propan-1-ol