Chloroacetyl chloride → HCID 6504217, compound

Participants

Reaction Steps

Aluminium chloride (III) (1.9 g, 14.25 mmol) was added portion wise at 0° C. to a solution of 3,4-dihydro-2H-1-benzopyran (9a) (450 mg, 3.35 mmol) and 2-chloroacetyl chloride (270 μL, 3.4 mmol) in dichloromethane (10 mL). After 3 hours, the mixture was quenched by a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (3×20 mL). The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/cyclohexane 40/60) to afford the desired product (9b) as a white yellow oil (250 mg, 1.19 mmol, 35%).

Provenance & Evidence