反应详情

To a solution of (S)-2,4-difluoro-6-(pent-4-en-2-yloxy)benzaldehyde (0.3394 g, 1.500 mmol) in THF (4 ml) at 0° C. was added dropwise, lithium aluminum hydride (0.900 ml, 1.800 mmol). The resulting mixture was stirred at rt for 2 h. The mixture was cooled to 0° C. and quenched dropwise with brine then diluted with EtOAc and water. The organic phase was washed with brine, dried (Na2SO4) and concentrated. The oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give (S)-(2,4-difluoro-6-(pent-4-en-2-yloxy)phenyl)methanol (0.1344 g, 0.589 mmol, 39.2% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ: 6.59-6.28 (m, 2H), 6.07-5.71 (m, 1H), 5.30-5.02 (m, 2H), 4.69 (d, J=5.6 Hz, 2H), 4.49 (sxt, J=6.0 Hz, 1H), 2.61-2.39 (m, 2H), 2.32 (t, J=6.8 Hz, 1H), 1.40 (d, J=6.1 Hz, 3H).

1. temperatureThe mixture was cooled to 0° C.
2. customquenched dropwise with brine
3. additionthen diluted with EtOAc and water
4. washThe organic phase was washed with brine
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV)