Dibenzylidene acetone → 1,5-Diphenylpentan-3-one
Reaction equation
[C:1]1([CH:7]=[CH:8][C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].C(OCC)(=O)C>[C:12]1([CH2:11][CH2:10][C:9](=[O:18])[CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1,5-Diphenyl-1,4-pentadien-3-one (20b, 1.00 g, 4.3 mmol) and palladium on activated carbon (0.25 g, 5%) were combined in ethyl acetate (50 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 2 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was chromatographed on silica gel with ethyl acetate/hexane to give 0.82 g (80%) of a clear oil; 1H NMR: δ 2.76 (t, 4H, J=7.6 Hz), 2.97 (t, 4H, J=7.4 Hz), 7.30 (m, 10H); 13C NMR: δ 29.6, 44.2, 125.8, 128.0, 128.2, 140.7, 208.4.