反应详情

温度

0 °C

LAH (1 M solution in ether, 7.74 mL) was added to a stirred solution of 4-(4-chloro-2-{[(triisopropylsilyl)oxy]methyl}phenyl)azetidin-2-one (0.7122 g, 1.935 mmol) in ether (2 mL) at 0° C. The solution was heated to reflux and after 2 h was cooled to 0° C. and quenched with water (0.294 mL), 15% sodium hydroxide solution (0.294 mL) and water (0.881 mL). The mixture was sonicated to give a uniform precipitate, filtered and evaporated in vacuo to an oil. The oil was dissolved in ethanol (10 mL) and concentrated HCl (0.167 mL, 2 mmol) was added with stirring at 0° C. The reaction was warmed to ambient temperature and after 30 min was evaporated in vacuo, azeotroping with ethanol to give (2-azetidin-2-yl-5-chlorophenyl)methanol hydrochloride (0.453 g) as a crystalline solid: 1H NMR (CD3OD, 400 MHz) δ 2.79 (m, 1H), 3.14 (m, 1H), 3.87 (dt, J=4.5 and 10.0 Hz, 1H, 4.18 (q, J=9.3 Hz, 1H), 4.61 (d, J=13.1 Hz, 1H), 4.68 (d, J=13.1 Hz, 1H), 5.93 (t, J=9.0 Hz, 1H), 7.49 (m, 2H), 7.69 (d, J=8.2 Hz, 1H).

1. temperatureThe solution was heated
2. temperatureto reflux and after 2 h
3. customquenched with water (0.294 mL), 15% sodium hydroxide solution (0.294 mL) and water (0.881 mL)
4. customThe mixture was sonicated
5. customto give a uniform precipitate
6. filtrationfiltered
7. customevaporated in vacuo to an oil
8. dissolutionThe oil was dissolved in ethanol (10 mL)
9. temperatureThe reaction was warmed to ambient temperature and after 30 min
10. customwas evaporated in vacuo
11. customazeotroping with ethanol