(1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether

Base Information

• Chemical Name: (1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether
• CAS No.: 217969-68-1
• Molecular Formula: C₁₈H₂₃BrO₂
• Molecular Weight: 351.283
• Mol file: 217969-68-1.mol

Synonyms:(1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether

Chemical Property of (1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether

There total 1 articles about (1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether 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: 50.0%

2,3-butadien-1-ol (18913-31-0) + (1R,2S)-2-phenylcyclohexyl vinyl ether (135500-31-1,127598-16-7) → (1R)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether (217969-74-9) + (1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether (217969-68-1)

Guidance literature:

With N-Bromosuccinimide;

DOI:10.1016/S0040-4039(98)01971-6

Reference yield:

(1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether (217969-68-1) → (2S,4R)-2-((1R,2S)-2-Phenyl-cyclohexyloxy)-4-vinyl-tetrahydro-furan + (2S,4S)-2-((1R,2S)-2-Phenyl-cyclohexyloxy)-4-vinyl-tetrahydro-furan (217969-81-8)

Guidance literature:

With air; triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at -78 ℃; for 3h;

DOI:10.1016/S0040-4039(98)01971-6

Reference yield:

(1S)-2-bromo-1-[(1R,2S)-(2-phenylcyclohexyl)oxy]ethyl 2,3-butadienyl ether (217969-68-1) → (S)-(+)-β-vinyl-γ-butyrolactone (107080-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent Chromat_. / Bu₃SnH, Et₃B, air / toluene; hexane / 3 h / -78 °C

2: 63 percent / HCl / tetrahydrofuran

3: 90 percent / PCC, Al₂O₃

With hydrogenchloride; aluminum oxide; air; triethyl borane; tri-n-butyl-tin hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/S0040-4039(98)01971-6

upstream raw materials:

2,3-butadien-1-ol

(1R,2S)-2-phenylcyclohexyl vinyl ether

Downstream raw materials:

(2S,4S)-2-((1R,2S)-2-Phenyl-cyclohexyloxy)-4-vinyl-tetrahydro-furan

(S)-(+)-β-vinyl-γ-butyrolactone