(E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane

Base Information

• Chemical Name: (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane
• CAS No.: 125536-52-9
• Molecular Formula: C₁₈H₂₈OSi
• Molecular Weight: 288.505
• Mol file: 125536-52-9.mol

Synonyms:(E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane

Chemical Property of (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane

There total 9 articles about (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane 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: 40.0%

4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-hept-2-ynoic acid ethyl ester (190258-58-3) → ethyl (Z)-(2-tert-butyldimethylsilyloxycyclopentylidene)acetate (77772-29-3) + (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane (125536-52-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; at 80 ℃;

DOI:10.1016/S0040-4020(97)00257-3

Reference yield: 32.0%

tert-butyl-<1-(3-iodopropyl)-3-phenylprop-2-ynyloxy>dimethylsilane (173728-39-7) → (Z)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane (125536-51-8) + (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane (125536-52-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In diethyl ether; at 80 ℃;

DOI:10.1016/S0040-4020(97)00257-3

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-1-tert-butyldimethylsilyloxy-2-phenylmethylenecyclopentane (125536-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / imidazole, dimethylaminopyridine, NaI / dimethylformamide / Ambient temperature

2: 1) BuLi / 1) THF, -50 deg C -> -20 deg C; -20 deg C, 15 min, 2) THF, -50 deg C -> 0 deg C, 2 h; 0 deg C, 3 h

3: 67 percent / I₂, 1,2-bis(diphenylphosphino)ethane / CH₂Cl₂ / Ambient temperature

4: Bu₃SnH, AIBN / diethyl ether / 80 °C

With 1H-imidazole; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; 1,2-bis-(diphenylphosphino)ethane; sodium iodide; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(97)00257-3

upstream raw materials:

benzyltrimethylsilane

2-(tert-Butyl-dimethyl-silanyloxy)-cyclopentanone

tert-butyl-<1-(3-iodopropyl)-3-phenylprop-2-ynyloxy>dimethylsilane

4-(tert-Butyl-dimethyl-silanyloxy)-7-iodo-hept-2-ynoic acid ethyl ester