tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane
• CAS No.: 146563-23-7
• Molecular Formula: C₂₃H₃₅IOSi
• Molecular Weight: 482.52
• Mol file: 146563-23-7.mol

Synonyms:tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane

Chemical Property of tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane

There total 13 articles about tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-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: 85.0%

2-[2-(tert-Butyl-dimethyl-silanyloxy)-2-(2-iodo-phenyl)-ethyl]-5-methyl-cyclohept-4-enone (146563-05-5) + Methylenetriphenylphosphorane (19493-09-5) → tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane (146563-23-7)

Guidance literature:

In tetrahydrofuran; at 23 ℃;

DOI:10.1021/ja00058a064

Reference yield:

4-(tert-Butyl-dimethyl-silanyloxy)-4-(2-iodo-phenyl)-1-(2-methyl-2-vinyl-cyclopropyl)-butan-1-one → tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane (146563-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: 2.) PPTS / 1.) PhH, reflux, 1.5 h, 2.) EtOH, H₂O, rt, 20 h

3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 0.5 h, 2.) 0 deg C to rt

With n-butyllithium; pyridinium p-toluenesulfonate; triethylamine; In dichloromethane;

DOI:10.1021/ja972427k

Reference yield:

2-iodobenzaldehyde (26260-02-6) → tert-Butyl-[1-(2-iodo-phenyl)-2-(4-methyl-7-methylene-cyclohept-3-enyl)-ethoxy]-dimethyl-silane (146563-23-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 96 percent / diethyl ether / 0 °C

2: 86 percent / imidazole / dimethylformamide

3: 1.) BH₃*SMe₂, 2.) H₂O₂, NaOH / 1.) hexane, 23 deg C

4: 85 percent / (COCl)2, DMSO, Et₃N / -60 °C

6: PCC, NaOAc / 3-Angstroem molecular sieves

7: Et₃N / CH₂Cl₂ / 0 °C

8: benzene / Heating

9: PPTS / ethanol; H₂O / 23 °C

10: 85 percent / tetrahydrofuran / 23 °C

With 1H-imidazole; sodium hydroxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00058a064

upstream raw materials:

2-[2-(tert-Butyl-dimethyl-silanyloxy)-2-(2-iodo-phenyl)-ethyl]-5-methyl-cyclohept-4-enone

Methylenetriphenylphosphorane

Methyltriphenylphosphonium bromide

2-iodobenzaldehyde

Downstream raw materials:

2-[2-(2-iodophenyl)2-oxoethyl]-5-methyl-1-methylenecyclohept-4-ene

2-[2-hydroxy-2-(2-iodophenyl)ethyl]-5-methyl-1-methylenecyclohept-4-ene