Methylhydrazine → O-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-hydroxylamine
Reaction equation
[C:1]([Si:5]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].CNN>ClCCl>[C:1]([Si:5]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[O:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][NH2:12])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
A solution of 2-[4-(tert-butyl-diphenyl-silanyloxy)-butoxy]-isoindole-1,3-dione (11.1 g, 23.4 mmol) in dichloromethane (100 ml) was treated with methylhydrazine. The reaction mixture was stirred overnight and was filtered. The filtrate was concentrated and purified by column chromatography [hexane/ethyl acetate (3.5/1)] to afford O-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-hydroxylamine (7.2 g, 90% yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.62-7.66(4H, m), 7.33-7.42 (6H, m), 3.64-3.68(4H), 1.54-1.70 (4H, m), 1.02 (9H, s); MS (APCI+)=344.2.