Methanol → 6-Decyl-3-hydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one

Participants

Reaction Steps

To a stirring solution of 3-hydroxy-6-decyl-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one (0.369 g, 0.7 mmol) in dichloromethane (20 ml) under Ar at 0° C. was added boron tribromide in dichloromethane (1.0M, 3.4 ml, 3.4 mmol, 5 equ). The mixture was warmed to room temperature and then stirred for 15 hours. Methanol (10 ml) was then added. The reaction was heated to reflux for 1 hour, then concentrated in vacuo to give a brown solid. Water (25 ml) was added and then extracted into ethyl acetate (3×). The organic layer was washed with brine then dried (MgSO4) and concentrated in vacuo to give 11g (0.318 g, 110%) as a brown oil.

Provenance & Evidence