Pyridine → (+/-)-3-Pyridylmethyl-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate

Participants

Reaction Conditions

Reaction Steps

A solution of (±)-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionyl chloride (4.3 g.) in benzene (20 ml.) is added, dropwise below 10° C., to a stirred solution of 3-pyridylmethanol (1.20 g.) and pyridine (1.10 g.) in benzene (20 ml.) and light petroleum (5 ml. b.p. 40°-60° C.). The mixture is stirred at 5° C. for 1 hour, and at ambient temperature for 18 hours. The mixture is filtered. The filtrate is diluted with ether, washed with water, aqueous sodium carbonate and water, dried with sodium sulphate, and evaporated to give an oil (4.1 g.). The oil is dissolved in a mixture of ethyl acetate, ethanol, and triethylamine (200:1:1) and is chromatographed on a column of silica gel (210 g.) made up in the same solvent. The column is eluted portionwise with the solvent. The first 350 ml. elutes an impurity (0.1 g.). The following 420 ml. of eluant is evaporated to give (±)-3-pyridylmethyl-2-(2-naphthylmethoxy)-3,3,3-trifluoro-2-methylpropionate (3.9 g.) as a syrup.

Provenance & Evidence