Dichloromethane → N-benzyl-O-benzylhydroxylamine hydrochloride
Reaction equation
[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]=1Participants
5
Procedure
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%).