1-(2,6-Dichlorophenyl)propan-2-one → 1175301-17-3
反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10](=[O:12])[CH3:11].[BH4-].[Na+]>CO.CCCCCC.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH:10]([OH:12])[CH3:11]参加物
5
実験手順
General Procedure GG: To a solution of 2,6-dichlorophenylacetone (500.00 mg, 2.46 mmol) in MeOH (5.0 mL) was added sodium borohydride (112 mg, 2.96 mmol) in small portions. The reaction mixture was allowed to stir overnight at rt. The reaction was monitored by TLC analysis on silica gel plates using Hexane/EtOAc (70:30) as eluent. The reaction mixture was quenched with aq. sat. NH4Cl (15 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine (20 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to give a colorless oil. The crude material was purified by silica gel chromatography using Hexane/EtOAc (70:30) as eluent to obtain the desired product as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=1.33 (d, J=6.1 Hz, 3H), 1.49 (d, J=5.3 Hz, 1H), 3.08-3.22 (m, 2H), 4.18-4.29 (m, 1H), 7.09-7.14 (m, 1H), 7.31 (s, 1H), 7.33 (s, 1H).