Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one → 5-Cyclopentyl-7-isopropyl-2,2-dimethyl-6-[4-(trifluoromethyl)benzyl]-2,3-dihydro-4H-chromen-4-one
Reaction equation
[C:1]1([C:6]2[C:15]([CH:16](O)[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([CH:28]([CH3:30])[CH3:29])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:32])([CH3:31])[O:11]3)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:6]2[C:15]([CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=3)=[C:14]([CH:28]([CH3:29])[CH3:30])[CH:13]=[C:12]3[C:7]=2[C:8](=[O:33])[CH2:9][C:10]([CH3:31])([CH3:32])[O:11]3)[CH2:2][CH2:3][CH2:4][CH2:5]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 60 mg (130 μmol) of 5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]-methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4H-chromen-4-one (Example 36A) and 14 mg of palladium-on-carbon (10%) in 10 ml of ethanol is stirred under a hydrogen atmosphere at atmospheric pressure overnight. The suspension is filtered through Celite, the filter cake is washed with ethanol and the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 40:1).