Benzyl Chloride → 2-(Benzyloxy)-N,N-dimethylbenzamide

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[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].C([O-])([O-])=O.[K+].[K+].[CH2:19](Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

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실험 절차

In an argon atmosphere, a mixture of 6.55 g (39.7 mmol) of 15, 10.9 g (79.3 mmol) of K2CO3, 1.0 g (5.94 mmol) of KI and 80 mL of anhydrous DMF was stirred for 10 min at room temperature. After that 7.52 g (59.5 mmol) of benzyl chloride was added in one portion. The resulting mixture was stirred for 2 hr at 70° C. and then evaporated to dryness. To the residue, 70 mL of water and 30 mL of dichloromethane were added. The organic layer was separated, and the aqueous layer was washed by 2×50 mL of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. The residue was washed by 50 mL of cold ether and dried in vacuum. Yield 9.71 g (96%) of a white solid.