Dichloromethane → N-benzyl-O-benzylhydroxylamine hydrochloride

반응식

[CH2:1]([O:8][N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[SiH](C)C1C=CC=CC=1.FC(F)(F)C(O)=O.[Cl:33]CCl>>[ClH:33].[CH2:10]([NH:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

참가 물질

반응물 4

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 13014Dimethylphenylsilane

HCID 561973O-benzylbenzaldoxime

생성물 1

HCID 18358890N-benzyl-O-benzylhydroxylamine hydrochloride수율 45%

실험 절차

To a solution of crude N-benzyloxybenzylideneamine from Example 22(a) (3.0 g, 14.2 mmol) in dichloromethane (30 mL) at 0° C. was added dimethylphenylsilane (3.09 mL, 20.3 mmol) followed by trifluoroacetic acid (3.92 mL, 50.6 mmol). The solution was allowed to warm to room temperature and was stirred for 16 hours. The solution was concentrated by rotary evaporation. To the crude oil was added dichloromethane (20 mL) and a hydrogen chloride saturated solution of dichloromethane (20 mL). The insoluble material (300 mg) was filtered and the solution was concentrated by rotary evaporation. To the crude oil was added a hydrogen chloride saturated solution of ether (20 mL). Additional ether (100 mL) was added and the insoluble material was filtered. The solid obtained was combined with the initial solid filtered above to give the title compound (1.57 g, 45%).