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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1719765Generated: October 27, 2026

tert-Butanol → (S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[(Z) 3-chloro-3-oxo-1-propenyl]-cyclopropane carboxylate

https://huagongshe.com/reaction/1719765

Reaction equation

Participants

RoleNameHCIDCharge
Reactanttert-ButanolHCID 6386—
Reactant1-Chloro-N,N-2-trimethylpropenylamineHCID 640792—
Reactant(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-carboxy-ethenyl]-cyclopropanecarboxylateHCID 13093798—
SolventDichloromethaneHCID 6344—
Product(S)alpha-cyano-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[(Z) 3-chloro-3-oxo-1-propenyl]-cyclopropane carboxylateHCID 13335684—

Reaction Conditions

Temperature20 °C

Reaction Steps

A solution of 0.25 ml of 1-chloro-N,N, 2-trimethyl-propenylamine, 7.5 ml of methylene chloride and 1.5 ml of tert.-butanol was added to a solution of 0.5 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-hydroxy -1-propenyl]-cyclopropane-carboxylate in 7.5 ml of methylene chloride and the mixtrue was stirred at 20° C. for 48 hours. The mixture was extracted with methylene chloride and the organic phase was washed with water and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 hexane-ether mixture to obtain 0.43 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis,Z) 2,2-dimethyl-3-[3-oxo-3-chloro-1-propenyl]-cyclopropane-carboxylate melting at 86° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04542142
Source datasetuspto-grants-1985_09
ORD IDord-7924213e06cc4a099ee9942466250de1
Source noteuspto-grants-1985_09