trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene

Base Information

• Chemical Name: trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene
• CAS No.: 120883-56-9
• Molecular Formula: C₂₇H₄₆O₂Si
• Molecular Weight: 430.747
• Mol file: 120883-56-9.mol

Synonyms:trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene

Chemical Property of trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene

There total 12 articles about trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene 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: 92.0%

trans-3-butyl-2-(4-(phenylmethoxy)butyl)cyclohexen-4-ol (120883-55-8) + tert-butyldimethylsilyl chloride (18162-48-6) → trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene (120883-56-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h;

DOI:10.1021/jo00275a023

Reference yield:

4-bromobutyl benzyl ether (60789-54-0) → trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene (120883-56-9)

Guidance literature:

Multi-step reaction with 8 steps

2: 1.) CeCl₃*7H₂O, NaBH₄ / 1.) methanol, -78 deg C, 2.) 0 deg C, 30 min

3: 98 percent / pyridine / 12 h / Ambient temperature

4: 95 percent / triethylamine, tetrakis(triphenylphosphine)palladium⁽⁰⁾ / tetrahydrofuran / 24 h / Heating

5: 72 percent / LiCl, LiOAc*2H₂O, Pd(OAc)2, p-benzoquinone / acetone / 8 h

6: 89 percent / CuCN / diethyl ether / 4 h / 0 °C

7: 98 percent / 5percent aq. MeOH, K₂CO₃ / 24 h / Ambient temperature

8: 92 percent / imidazole / dimethylformamide / 3 h / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; palladium diacetate; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; lithium acetate; potassium carbonate; triethylamine; p-benzoquinone; lithium chloride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00275a023

Reference yield:

trans-2-butyl-3-hydroxy-1-cyclohexanone (120883-61-6) → trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(phenylmethoxy)butyl)cyclohexene (120883-56-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / imidazole / dimethylformamide / 3 h / Ambient temperature

2: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) 12 h

3: 1.) copper(I) iodide / 1.) THF, -78 deg C, 30 min, 2.) -20 deg C, 12 h

With 1H-imidazole; copper(l) iodide; lithium diisopropyl amide; In N,N-dimethyl-formamide;

DOI:10.1021/jo00275a023

upstream raw materials:

4-(phenylmethoxy)butyllithium

trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)cyclohexen-2-yl trifluoromethanesulfonate

trans-3-butyl-2-(4-(phenylmethoxy)butyl)cyclohexen-4-ol

tert-butyldimethylsilyl chloride

Downstream raw materials:

4-(1-(trans-5-((tert-butyldimethylsilyl)oxy)-6-butylcyclohexenyl))butanol

trans-3-butyl-4-((tert-butyldimethylsilyl)oxy)-2-(4-(N-(phenylmethyl)amino)butyl)cyclohexene

(6S*,7S*,8S*,11S*)-7-butyl-8-((tert-butyldimethylsilyl)oxy)-11-iodo-1-(phenylmethyl)-1-azaspiro<5.5>undecane

Toluene-4-sulfonic acid 4-[(5R,6R)-6-butyl-5-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-butyl ester