反应详情

温度

0 °C

To a solution of (R)-ethyl 5-((tert-butyldiphenylsilyl)oxy)hexanoate (10 g, 25.09 mmol) in THF (150 mL) at 0° C. was added dropwise 1M LAH in THF (31.4 mL, 31.4 mmol) and the resulting mixture was stirred for 30 min. at 0° C. and then 2 h at room temp. The reaction was quenched with 1 mL of water (stir for 10 min), 1 mL of 15% NaOH/water (stir for 10 min), and then 2 mL of water. After stirring for 1 h, the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried under high vacuum for 16 h to afford (R)-5-((tert-butyldiphenylsilyl)oxy)hexan-1-ol (8.9 g, 24.96 mmol, 99% yield) as a clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.72-7.67 (m, 4H), 7.50-7.36 (m, 6H), 3.92-3.84 (m, 1H), 3.61-3.50 (m, 2H), 1.55-1.41 (m, 4H), 1.37-1.31 (m, 2H), 1.21-1.15 (m, 1H), 1.11-1.09 (m, 3H), 1.08 (s, 9H).

1. custom2 h
2. customat room temp
3. customThe reaction was quenched with 1 mL of water (stir for 10 min), 1 mL of 15% NaOH/water (stir for 10 min)
4. stirringAfter stirring for 1 h
5. filtrationthe mixture was filtered through celite
6. concentrationThe filtrate was concentrated in vacuo
7. customThe residue was dried under high vacuum for 16 h