Water → HCID 68488610, compound

Participants

Reaction Steps

While stirring a solution of 6-chloro-4-(3-hydroxypropyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one (1.0 g, 3.23 mmol) in acetone (20 mL), Jones reagent (8 N chromic acid, H2SO4—H2O solution, 2 mL) was added dropwise thereto at room temperature. Then water (20 mL) was added thereto and the solution was stirred at room temperature for 3 hours. Then, to the reaction solution, 2-propanol was added and the solution was stirred at room temperature for 5 minutes. After the reaction solution was diluted with ethyl acetate, a 8 N aqueous sodium hydroxide solution was added thereto, and the aqueous layer was separated. After the aqueous layer was acidified by adding 8 N hydrochloric acid thereto, the solution was diluted with ethyl acetate and the organic layer was separated. The organic layer was washed with water and saturated brine, and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure, whereby the objective compound (726 mg, 70%) was obtained as a pale yellow solid.

Provenance & Evidence