反应 #76472

反应方程式

6-vinylchroman

THF

9-BBN

→

6-(2-hydroxyethyl)chroman

收率 24.0%

反应条件

后处理

1. 1
   温度The reaction mixture was heated
2. 2
   温度to reflux for 8 h
3. 3
   其他The reaction was quenched with water (1.5 mL)
4. 4
   workup.ADDITIONtreated with NaBO3.4H2O
5. 5
   萃取Diethyl ether (4 mL) and the reaction mixture were extracted with CH2Cl2 (2×20 mL)
6. 6
   浓缩The organic layers were concentrated to a clear oil that
7. 7
   其他was purified by silica gel chromatography
8. 8
   洗涤eluting with ethyl acetate (50%, v/v) in hexane

实验过程

A solution of the 6-vinylchroman intermediate (0.12 g, 0.27 mmol) in anhydrous THF (1 mL) was cooled to 0° C. and treated with 9-BBN (0.60 mL, 0.5 M in THF, 0.3 mmol). The reaction mixture was heated to reflux for 8 h. The reaction was quenched with water (1.5 mL) and treated with NaBO3.4H2O and the resulting slurry was stirred overnight. Diethyl ether (4 mL) and the reaction mixture were extracted with CH2Cl2 (2×20 mL). The organic layers were concentrated to a clear oil that was purified by silica gel chromatography eluting with ethyl acetate (50%, v/v) in hexane. This yielded the desired 6-(2-hydroxyethyl)chroman intermediate as a colorless oil (30 mg, 24%). 1H-NMR (CDCl3/TMS, ppm): 0.87 (m, 12H, 4a′-, 8a′-, 12a′-, 13′-CH3), 1.0-1.6 (m, 24H, 4′-, 8′-, 12′-CH, 1′-, 2′-, 3′-, 5′-, 6′-, 7′-, 9′-, 10′-, 11′-CH2, 2a-CH3), 1.81 (m, 2H, 3-CH2), 2.17, 2.24, 2.28 (3×s, 9H, 5a-, 7a-, 8a-CH3), 2.68 (t, J=6.8 Hz, 2H, 4-CH2), 3.01 (t, J=7.5 Hz, 2H, Ar—CH2), 3.74 (t, J=7.5 Hz, 2H, OCH2); 13C-NMR (CDCl3, ppm): 12.0, 15.1, 16.0 (5a-, 7a-, 8a-CH3), 19.6, 19.7 (CH3), 20.6, 21.0 (CH2), 22.6, 22.7 (CH3), 23.8 (2a-CH3), 24.4, 24.8 (CH2), 28.0 (CH), 31.2 (3-CH2), 32.7, 32.8 (CH), 37.3, 37.4, 37.5, 39.4, 40.0 (CH2), 62.2 (OCH2), 72.6 (2-C), 116.8, 122.3, 124.9, 132.4, 133.9 (aryl C), 150.1 (aryl C—O); HRMS (CI, m/z): 458.412154 (M+H+, Calc. for C31H54O2 458.412384).

来源