(-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one

Base Information

• Chemical Name: (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one
• CAS No.: 1380438-77-6
• Molecular Formula: C₁₄H₁₃ClO₂
• Molecular Weight: 248.709
• Mol file: 1380438-77-6.mol

Synonyms:(-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one

Chemical Property of (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one

There total 2 articles about (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one 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: 42.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + (E)-4-(4-chlorophenyl)but-3-en-2-yl acetate (99512-15-9) → (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one (1380438-77-6) + (-)-(S)-(E)-4-(4-chlorophenyl)but-3-en-2-yl acetate

Guidance literature:

(furan-2-yloxy)-trimethylsilane; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

(E)-4-(4-chlorophenyl)but-3-en-2-yl acetate; In dichloromethane; at 0 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Resolution of racemate;

DOI:10.1002/anie.201109075

Reference yield:

(E)-4-(4-chlorophenyl)but-3-en-2-ol (32271-56-0,134747-46-9,77209-44-0) → (-)-(R)-(E)-3-(4-(4-chlorophenyl)but-3-en-2-yl)furan-2(5H)-one (1380438-77-6) + (-)-(S)-(E)-4-(4-chlorophenyl)but-3-en-2-yl acetate

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere; Resolution of racemate

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; In dichloromethane;

DOI:10.1002/anie.201109075

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

(E)-4-(4-chlorophenyl)but-3-en-2-yl acetate

(E)-4-(4-chlorophenyl)but-3-en-2-ol