反应详情

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0 °C

(5-(Trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol To a solution of 5-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-7-carbaldehyde (1 g, 2.9 mmol) in ethanol (15 mL) at 0° C. was added sodium borohydride (0.055 g, 1.45 mmol). The ice bath was removed and stirring continued for 15 min. The reaction was cooled to 0° C. and quenched by addition of saturated ammonium chloride. The reaction was concentrated to remove most of the ethanol and poured into diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated to give 0.985 g (98%) as an oil which solidified upon standing. 1H-NMR (CDCl3, 500 MHz) δ 8.08 (s, 1H), 8.00 (s, 1H), 7.57 (d, J=1.2 Hz, 1H), 5.96 (s, 2H), 5.07 (s, 2H), 3.53 (m, 2H), 3.34 (bs, 1H), 0.85 (m, 2H), −0.08 (s, 9H); 13C-NMR (CDCl3, 126 MHz) δ 139.0, 135.1, 125.9, 125.3, 124.52 (q, J=272 Hz), 124.51, 124.2 (q,J=33 Hz), 119.3, 80.1, 66.7, 62.6, 17.8, −1.5.

1. customThe ice bath was removed
2. customquenched by addition of saturated ammonium chloride
3. concentrationThe reaction was concentrated
4. customto remove most of the ethanol
5. additionpoured into diethyl ether
6. washThe ethereal was washed with water (2×)
7. dry with materialbrine, dried over magnesium sulfate
8. concentrationconcentrated
9. customto give 0.985 g (98%) as an oil which