Dicyclohexylcarbodiimide → 3-benzyl-4-fluorobenzyl (1RS, cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate

A solution of dicyclohexylcarbodiimide (0.4 g) in dichloromethane (10 cm3) was added to a stirred mixture of (1RS, cis)-3-(Z-2-chloro,3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid (0.54 g), 3-benzyl-4-fluorobenzyl alcohol (0.43 g), 4-dimethylaminopyridine (0.02 g) and dry dichloromethane (5 cm3), and the resultant mixture stirred at the ambient temperature (ca. 20° C.) for 18 hours. The reaction mixture was then heated to the reflux temperature for 3 hours, and subsequently cooled again. The precipitate which formed was removed by filtration, and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residual oil was purified by column chromatography using a silica column eluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60°-80° C., 19 parts by volume), to yield 3-benzyl-4-fluorobenzyl (1RS, cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylate (0.32 g).

1. temperatureThe reaction mixture was then heated to the reflux temperature for 3 hours
2. temperaturesubsequently cooled again
3. customThe precipitate which formed
4. customwas removed by filtration
5. concentrationthe filtrate concentrated by evaporation of the solvent under reduced pressure
6. customThe residual oil was purified by column chromatography
7. washeluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60°-80° C., 19 parts by volume)

ORD 기록

ord-53fb8ab458444caba6012fc5c7d54fcf

출처 데이터셋

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04902814