{2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol

Base Information

• Chemical Name: {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol
• CAS No.: 888325-02-8
• Molecular Formula: C₂₁H₃₄O₂Si
• Molecular Weight: 346.585
• Mol file: 888325-02-8.mol

Synonyms:{2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol

Chemical Property of {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol

There total 16 articles about {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol 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: 60.0%

1-(tert-butyldimethylsilyloxymethyl)-2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]benzene (888325-01-7) → {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol (888325-02-8)

Guidance literature:

With (1S)-10-camphorsulfonic acid; In methanol; dichloromethane; at 0 ℃; for 1.66667h;

DOI:10.1021/ol0604264

Reference yield:

2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]ethanol (888324-77-4) → {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol (888325-02-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 93 percent / LiBr; Et₃N; methanesulfonyl chloride / tetrahydrofuran / 144 h / 20 °C

2.1: NaH / tetrahydrofuran / 20 °C

2.2: 80 percent / NaI / acetonitrile / 12 h / 60 °C

3.1: 93 percent / LiAlH₄ / diethyl ether / 5 h / 0 - 20 °C

4.1: 58 percent / NaH; tetrabutylamminium iodide / tetrahydrofuran; dimethylsulfoxide / 0 - 20 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: 1.16 g / tetrahydrofuran / 1 h / 0 °C

7.1: 84 percent / imidazole / dimethylformamide / 23 h / 20 °C

8.1: 77 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 1 h / 20 °C

9.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

10.1: 157 mg / n-BuLi / tetrahydrofuran; hexane / -15 - 20 °C

11.1: 60 percent / (1S)-(+)-⁽¹⁰⁾-camphorsulfonic acid / CH₂Cl₂; methanol / 1.67 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; (1S)-10-camphorsulfonic acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Swern oxidation / 9.1: Swern oxidation / 10.1: Wittig olefination;

DOI:10.1021/ol0604264

Reference yield:

[2-(2-bromo-ethyl)-benzyloxy]-tert-butyl-dimethyl-silane (951776-91-3) → {2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]phenyl}methanol (888325-02-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 20 °C

1.2: 80 percent / NaI / acetonitrile / 12 h / 60 °C

2.1: 93 percent / LiAlH₄ / diethyl ether / 5 h / 0 - 20 °C

3.1: 58 percent / NaH; tetrabutylamminium iodide / tetrahydrofuran; dimethylsulfoxide / 0 - 20 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: 1.16 g / tetrahydrofuran / 1 h / 0 °C

6.1: 84 percent / imidazole / dimethylformamide / 23 h / 20 °C

7.1: 77 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 1 h / 20 °C

8.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

9.1: 157 mg / n-BuLi / tetrahydrofuran; hexane / -15 - 20 °C

10.1: 60 percent / (1S)-(+)-⁽¹⁰⁾-camphorsulfonic acid / CH₂Cl₂; methanol / 1.67 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; (1S)-10-camphorsulfonic acid; water; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Swern oxidation / 8.1: Swern oxidation / 9.1: Wittig olefination;

DOI:10.1021/ol0604264

upstream raw materials:

1-(tert-butyldimethylsilyloxymethyl)-2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]benzene

2-[2-((tert-butyldimethylsilanyloxy)methyl)phenyl]ethanol

[2-(2-bromo-ethyl)-benzyloxy]-tert-butyl-dimethyl-silane

2-(2-((tert-butyldimethylsilyloxy)methyl)phenethyl)propane-1,3-diol

Downstream raw materials:

Se-phenyl 2-[4-(tert-butyldimethylsilyloxy)-3-vinylhex-5-enyl]benzoselenoate