反应详情

To a suspension of LiAlH4 (280 mg, 7.37 mmol) in dry tetrahydrofuran (20 mL) under nitrogen atmosphere, a solution of 75 (1.0 g, 3.83 mmol) in THF (10 mL) was added and the mixture was refluxed for 3 h. After cooling, the excess of LiAlH4 was destroyed with a saturated solution of sodium sulfate. The mixture was filtered on MgSO4 and the filtrate concentrated in vacuo. The residue was partitioned between water (30 mL) and CH2Cl2 (30 mL). The aqueous-phase was separated and extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was dissolved in Et2O (5 mL) and treated with HCl/Et2O. The precipitated hydrochloride salt was filtered and triturated with dry Et2O (3×2 mL), obtaining 760 mg of product (yield 70%). 1H NMR (CD3OD, 300 MHz) δ 7.50-7.33 (m, 7H), 7.15 (d, J=9 Hz, 1H), 5.22 (s, 2H), 4.13 (s, 2H). MS (m/e) (API-ES) 248 (M−Cl)+. m.p 119-121° C.

1. temperaturethe mixture was refluxed for 3 h
2. temperatureAfter cooling
3. customthe excess of LiAlH4 was destroyed with a saturated solution of sodium sulfate
4. filtrationThe mixture was filtered on MgSO4
5. concentrationthe filtrate concentrated in vacuo
6. customThe residue was partitioned between water (30 mL) and CH2Cl2 (30 mL)
7. customThe aqueous-phase was separated
8. extractionextracted with CH2Cl2 (20 mL×2)
9. dry with materialThe combined organic phases were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. dissolutionThe residue was dissolved in Et2O (5 mL)
13. additiontreated with HCl/Et2O
14. filtrationThe precipitated hydrochloride salt was filtered
15. customtriturated with dry Et2O (3×2 mL)