Thionyl Chloride → (1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride

HRID 569517Notes

Reaction equation

HRID 569517 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[C:17](O)=[O:18].S(Cl)([Cl:23])=O>C=CC(=C)C>[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C@H:3]1[C:17]([Cl:23])=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70420059(1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane carboxylic acid

Product 1

HCID 88650986(1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride

Reagents, catalysts & solvents 1

HCID 6557IsopreneSolvent

Procedure

A mixture of 1.6 g of (1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane carboxylic acid, 10 ml of isoprene and 1 ml of thionyl chloride was stirred for 5 hours under a current of nitrogen and then was concentrated to obtain 2 g of (1R,cis)2,2-dimethyl-3[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride which was concentrated to obtain 2 g of (1R,cis)2,2-dimethyl-3-[(Z)3-oxo-3-benzyloxy-1-propenyl]-cyclopropane-carboxylic acid chloride which was used as is in the following step.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-34d6dab6b5a54605a94d29924c9e4995
Source dataset
uspto-grants-1988_03
Patent number
US04732903

Reaction notes

Loading…