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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1719741Generated: October 27, 2026

Dichloromethane → (S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate

https://huagongshe.com/reaction/1719741

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
Reactant(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 9837437—
Reactant(1R,cis)2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylic acidHCID 13093792—
SolventPyridineHCID 1049—
Product(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylateHCID 1309379476.3%

Reaction Steps

6.2 g of dicyclohexycarbodiimide were added to a solution of 9.5 g of the product of Step C, 30 ml of methylene chloride and 3 ml of pyridine and the reaction mixture was stirred for half an hour. 6.8 g of (S)α-cyano-3-phenoxy-benzyl alcohol were added thereto and the mixture was stirred for an hour and half and filtered. The filtrate was washed with N hydrochloric acid, then with water until neutral, dried, and evaporated to dryness. The 15.3 g of oil residue were chromatographed over silica gel and eluted with a 97-3 mixture of benzene-ethyl acetate to obtain 12 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonylethynyl)-cyclopropane-carboxylate melting at 101° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04542142
Source datasetuspto-grants-1985_09
ORD IDord-6a240de6243f44c2b32fec98f0f45fd0
Source noteuspto-grants-1985_09