Tetrabutylammonium Fluoride → N-(2-(1,3-Dioxolan-2-yl)ethyl)-N-(2-hydroxyethyl)acetamide

반응식

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][CH2:13][O:14][Si](C(C)(C)C)(C)C)[C:9](=[O:11])[CH3:10].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][N:8]([CH2:12][CH2:13][OH:14])[C:9](=[O:11])[CH3:10]

참가 물질

실험 절차

To a stirred solution of N-(2-(1,3-dioxolan-2-yl)ethyl)-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)acetamide (0.65 g, 2.04 mmol) in THF (5 mL) was added a solution of tetrabutylammonium fluoride (1.0 M in THF, 2.24 mL). The reaction mixture was stirred at RT for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The combined organic extracts were dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was purified by flash column chromatography eluting with 0 to 100% ethyl acetate/iso-hexane to afford the title compound (0.287 g, 69%) which was used directly in the next step.