反应详情

温度

0 °C

LiAlH4 (0.154 g, 4.06 mmol) was suspended in anhydrous Et2O (10 mL) under a N2 atmosphere and cooled (0° C.) with stirring. Anhydrous AlCl3 (1.08 g, 8.14 mmol)was dissolved in ice-cold anhydrous Et2O (20 mL) and added dropwise to the LiAlH4 suspension. After complete addition the suspension was stirred at the same temperature (20 min.). (2-Bromo-phenyl)-(3-methoxy-phenyl)-methanol [13] (0.68 g, 2.32 mmol) was dissolved in anhydrous Et2O (10 mL) and added dropwise via syringe to the suspension. After complete addition the reaction mixture was heated at reflux (4 h), cooled (0° C.) and EtOAc was added dropwise to destroy the excess of the reagent and the mixture was added to 20% aq. H2SO4 (50 mL). Et2O (50 mL) was added and extracted. The Et2O layer was separated, washed with water, brine, dried (MgSO4) and evaporated to give a reddish yellow oil. The oil was purified by mplc using pet. ether-CH2Cl2 (9:1) as eluent to give 0.485 g (75%) of the pure product as a colorless oil. 1H NMR (CDCl3)d: 3.81 (s, 3H, CH3), 4.14 (s, 2H, CH2), 6.79-7.62 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 42.34, 55.69, 112.07, 122.02, 125.48, 128.07, 128.50, 130.02, 131.66, 133.43.

1. additionAfter complete addition the suspension
2. stirringwas stirred at the same temperature (20 min.)
3. additionadded dropwise via syringe to the suspension
4. additionAfter complete addition the reaction mixture
5. temperaturewas heated
6. temperatureat reflux (4 h)
7. additionwas added dropwise
8. customto destroy the excess of the reagent
9. additionthe mixture was added to 20% aq. H2SO4 (50 mL)
10. additionEt2O (50 mL) was added
11. extractionextracted
12. customThe Et2O layer was separated
13. washwashed with water, brine
14. dry with materialdried (MgSO4)
15. customevaporated
16. customto give a reddish yellow oil
17. customThe oil was purified by mplc