(+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene

Base Information

• Chemical Name: (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene
• CAS No.: 126901-34-6
• Molecular Formula: C₁₃H₂₅BrOSi
• Molecular Weight: 305.33
• Mol file: 126901-34-6.mol

Synonyms:(+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene

Chemical Property of (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene

There total 2 articles about (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene 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: 93.0%

(+/-)-2-bromo-3-methylcyclohex-2-en-1-ol (126901-33-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene (126901-34-6)

Guidance literature:

With 1H-imidazole; In diethyl ether; for 12h;

DOI:10.1021/jo00300a015

Reference yield:

α-bromo-3-methylcyclohex-2-en-1-one (51326-26-2) → (+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene (126901-34-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / LiAlH₄ / diethyl ether / 1. -78 deg C, 20 min 2. 0 deg C, 30 min

2: 93 percent / imidazole / diethyl ether / 12 h

With 1H-imidazole; lithium aluminium tetrahydride; In diethyl ether;

DOI:10.1021/jo00300a015

Reference yield:

(+/-)-2-bromo-1-<(tert-butyldimethylsilyl)oxy>-3-methylcyclohex-2-ene (126901-34-6) → (4R,10S)-(-)-(5E,7Z)-9,10-secocholesta-5,7,14-trien-4-ol (126901-31-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1. t-BuLi 2. I₂ / 1. pentane, ether, -50 deg C, 2 h 2. 15 min

2: 1. EtMgBr / 2. Pd(PPh₃)4 / 1. THF, 1 h , reflux 2. benzene, reflux, 16 h

3: 72 percent / n-Bu₄NF / tetrahydrofuran / 16 h

4: 49 percent / H₂, quinoline / Lindlar catalyst / hexane / 2 h

5: 2,2,4-trimethyl-pentane / 98.5 °C

With quinoline; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; Lindlar's catalyst; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane;

DOI:10.1021/jo00300a015

upstream raw materials:

(+/-)-2-bromo-3-methylcyclohex-2-en-1-ol

tert-butyldimethylsilyl chloride

α-bromo-3-methylcyclohex-2-en-1-one

Downstream raw materials:

(+/-)-1-<(tert-butyldimethylsilyl)oxy>-2-iodo-3-methylcyclohex-2-ene

(4R,10S)-(-)-(5E,7Z)-9,10-secocholesta-5,7,14-trien-4-ol

(4R,10R)-(-)-(5E,7Z)-9,10-secocholesta-5,7,14-trien-4-ol

(4S,10R)-(-)-(5E,7Z)-9,10-secocholesta-5,7,14-trien-4-ol