Acetic Acid → HCID 6496944, compound

Participants

Reaction Steps

To a solution of 4-phenoxybenzaldehyde (4.4 ml, 25 mmol) in ethanol (50 ml) was added methylamine (3.0 ml of 33% solution in ethanol, 25 mmol) and acetic acid (1.4 ml, 25 mmol), and the mixture was stirred under an atmosphere of nitrogen. After 20 minutes sodium tri(acetoxy)borohydride (10.5 g, 50 mmol) was added and stirring was continued for 16 hours. The mixture was diluted with 2 M aqueous hydrochloric acid (200 ml) and washed with diethyl ether (2×100 ml). The aqueous layer was basified to pH 12 with concentrated aqueous ammonia solution and extracted with dichloromethane (4×100 ml). The combined organic layers were dried (Na2SO4), the solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (dichloromethane/methanol/aqueous ammonia solution 95:5:0 to 94:5:1) to give the titled compound as a colourless oil (3.3 g).

Provenance & Evidence