反应详情

To a solution of pent-4-en-2-yl 4-chloro-2-((S)-pent-4-en-2-yloxy)benzoate (1.36 g, 4.40 mmol) in THF (15 ml) that was cooled to 0° C. was added dropwise over 30 min lithium aluminum hydride (2.64 ml, 5.28 mmol) and the resulting mixture was stirred at rt. After 3 h, the mixture was cooled to 0° C. and quenched by dropwise addition of brine. The mixture was diluted with EtOAc and the organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give (S)-(4-chloro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.9554 g, 4.21 mmol, 96% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.21 (d, J=7.8 Hz, 1H), 6.98-6.88 (m, 1H), 6.88 (d, J=1.7 Hz, 1H), 5.86 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.25-5.06 (m, 2H), 4.75-4.62 (m, 1H), 4.62-4.43 (m, 2H), 2.61-2.40 (m, 2H), 2.34 (t, J=6.5 Hz, 1H), 1.38 (d, J=6.1 Hz, 3H).

1. temperaturethe mixture was cooled to 0° C.
2. customquenched by dropwise addition of brine
3. additionThe mixture was diluted with EtOAc
4. washthe organic phase was washed with brine
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV)