Diisopropylamine → 2-(3-Chloro-2,4,5-trifluorophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

Participants

Reaction Steps

A solution of 7.6 mL (54.2 mmol) of diisopropylamine in 100 mL of dry THF was cooled to -78° C. under argon, treated with 20.5 mL (47.2 mmol) of 2.3M n-butyllithium, and stirred for 15 minutes. To this solution was added a solution of 10.3 g (45.0 mmol) of 2-(2,4,5-trifluorophenyl)-4, 4-dimethyl-2-oxazoline in 100 mL of dry THF. The reaction mixture was stirred at -78° C. for 45 minutes. To this mixture was added 26.5 g (100 mmol) of hexachloroacetone, and the solution was warmed to room temperature. Water was added; the organic phase was washed with water, 1N hydrochloric acid, and 5% sodium bicarbonate, and was dried over magnesium sulfate. Concentration gave a dark oil which was chromatographed on silica gel to give 7.05 g of the title compound as a yellow oil.

Provenance & Evidence