Sodium hydride → HCID 14012521, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.0 g of 7-chloro-6-hydroxy-3-(2-fluorophenyl)-1,2-benzisoxazole in 30 ml dimethylformamide is added to a suspension of 1 g (50% suspension in oil) sodium hydride in 30 ml of dimethylformamide with stirring. Bromoacetaldehyde diethylacetal (6.2 ml) is added and the reaction mixture is heated at 80° C. for 24 hrs. The resulting dark solution is poured onto ice/water and extracted with four-100 ml portions of ether. The combined ether extracts are washed with dilute sodium hydroxide solution, saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent followed by recrystallization from ether/petroleum ether affords {[7-chloro-3(2-fluorophenyl)-1,2-benzisoxazol-6-yl]oxy}acetaldehyde diethyl acetal as white needles, mp 59° C.

Provenance & Evidence