反应详情

To a solution of 1-(4-(2-(ethoxymethoxy)propan-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-lan-2-yl)phenyl)ethanone (684 mg, 1.89 mmol) in THF (15 mL) was added 6N HCl (10 mL). The reaction mixture was stirred at rt overnight. Water was added and the mixture was extracted with EA. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE-EA (5:1) to give 1-(1-hydroxy-3,3-dimethyl-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)ethanone (324 mg; yield 50% over 2 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.26 (b, 1H), 8.29 (s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 2.61 (s, 3H), 1.44 (s, 6H) ppm; MS: m/z=205.1 (M+1, ESI+).

1. extractionthe mixture was extracted with EA
2. washThe organic layers were washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography over silica gel
7. washeluted with PE-EA (5:1)