2-(4-benzyloxy-3,5-dimethoxy-phenyl)-1-(2,2-dimethyl-2H-chromen-6-yl)-ethanone → 1-(2,2-Dimethyl-chroman-6-yl)-2-(4-hydroxy-3,5-dimethoxy-phenyl]-ethanone
Reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][C:18]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[O:26][C:25]([CH3:31])([CH3:30])[CH:24]=[CH:23]3)=[O:19])=[CH:11][C:10]=1[O:32][CH3:33])C1C=CC=CC=1>CO.[Pd]>[CH3:30][C:25]1([CH3:31])[CH2:24][CH2:23][C:22]2[C:27](=[CH:28][CH:29]=[C:20]([C:18](=[O:19])[CH2:17][C:12]3[CH:13]=[C:14]([O:15][CH3:16])[C:9]([OH:8])=[C:10]([O:32][CH3:33])[CH:11]=3)[CH:21]=2)[O:26]1Participants
4
Procedure
To a solution of 2-(4-benzyloxy-3,5-dimethoxy-phenyl)-1-(2,2-dimethyl-2H-chromen-6-yl)-ethanone (62.8 mg) dissolved in methanol (5.0 mL) and hexanes (3.3 mL) was added palladium on carbon (19.13 mg, 10% on carbon). The reaction mixture was purged with nitrogen numerous times before being exposed to a hydrogen atmosphere. Hydrogenation proceeded at room temperature and at atmospheric pressure. After 15 minutes, the reaction was purged again with nitrogen and the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated to yield the desired product.