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

HRID 1719735Notes

Reaction equation

HRID 1719735 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 in the following step.

Workup

  1. concentrationwas concentrated

Sources & evidence

ORD record
ord-99f0a8740da24914846e1ee4cc9a8efb
Source dataset
uspto-grants-1985_09
Patent number
US04542142

Reaction notes

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