3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone

Base Information

• Chemical Name: 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone
• CAS No.: 169131-87-7
• Molecular Formula: C₁₃H₁₂Cl₂O₂
• Molecular Weight: 271.143
• Mol file: 169131-87-7.mol

Synonyms:3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone

Chemical Property of 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone

There total 2 articles about 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone 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: 70.0%

(1'R)-phenyl 2'-propenyl 2-butynoate (169131-88-8) → 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone (169131-87-7)

Guidance literature:

With bis(benzonitrile)palladium(II) dichloride; lithium chloride; copper dichloride; In acetonitrile;

DOI:10.1016/0957-4166(95)00210-G

Reference yield:

(R)-1-phenylprop-2-en-1-ol (104713-12-4) → 3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone (169131-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: DCC, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

2: 70 percent / CuCl₂, LiCl, PdCl₂(PhCN)2 / acetonitrile

With dmap; bis(benzonitrile)palladium(II) dichloride; dicyclohexyl-carbodiimide; lithium chloride; copper dichloride; In dichloromethane; acetonitrile;

DOI:10.1016/0957-4166(95)00210-G

Reference yield:

3-(Z)-chloroethylidene-4S-chloromethyl-5R-phenyl-γ-butyrolactone (169131-87-7) → (3S,4R)-4-Benzyl-3-ethyl-dihydro-furan-2-one + (3R,4R)-4-Benzyl-3-ethyl-dihydro-furan-2-one

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; In methanol; for 24h; under 4560 Torr; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0957-4166(95)00210-G

upstream raw materials:

(1'R)-phenyl 2'-propenyl 2-butynoate

(R)-1-phenylprop-2-en-1-ol