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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1995162Generated: 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/1995162

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
ReactantDicyclohexylcarbodiimideHCID 10868—
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 13093794—

Reaction Steps

6.2 g of dicyclohexylcarbodiimide were added to a mixture of 9.5 g of the product of Step B, 30 ml of methylene chloride and 3 ml of pyridine and after stirring for 30 minutes, 6.8 g of (S)α-cyano-3-phenoxy-benzyl alcohol were added to the mixture. The mixture was stirred for 90 minutes and was filtered and the filtrate was washed with N hydrochloric acid and then with water until the wash water was neutral, dried and evaporated to dryness. The 16.3 g of oil residue were chromatographed over silica gel and eluted with a 97-3 benzene-ethyl acetate mixture to obtain 12 of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-(2,2,2-trichloroethoxycarbonyl-ethynyl]-cyclopropane-carboxylate melting at 101° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04402972
Source datasetuspto-grants-1983_09
ORD IDord-166a440e0ec0445e84f1ebfad7dea3f0
Source noteuspto-grants-1983_09