反应详情

温度

0 °C

To the ketone from example 39 (1.34 g, 5.4 mmol) dissolved in dry THF (20 ml), cooled to 0° C., was added sodium borohydride (308 mg, 8.1 mmol) portionwise. The reaction mixture was stirred for 2 hours then 3M NaOH (aq) (10 ml) was added and stirring continued for a further 16 hours. The reaction mixture was extracted with ethyl acetate (2×20 ml) and the combined organic extracts washed with brine (5 ml), dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica eluting with ethyl acetate:pentane (1:5) to give the title compound as a colourless oil (900 mg, 4.2 mmol, 78%). 1H NMR (CDCl3, 400 MHz) δ: 2.13 (s, 6H), 2.91 (dd, 1H), 3.25 (t, 1H), 3.98 (t, 1H), 5.90 (s, 2H) 7.20 (d, 1H), 7.62 (dd, 1K), 8.58 (s, 1H). LRMS: m/z 215 (M-H+).

1. stirringstirring
2. waitcontinued for a further 16 hours
3. extractionThe reaction mixture was extracted with ethyl acetate (2×20 ml)
4. washthe combined organic extracts washed with brine (5 ml)
5. dry with materialdried over anhydrous magnesium sulphate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography on silica eluting with ethyl acetate:pentane (1:5)