反应详情

To a mixture of 2.0 M of ammonia in ethanol (117 mL, 235 mmol, Aldrich, Cat. No. 392685) and titanium tetraisopropoxide (27.7 mL, 93.9 mmol, Aldrich, Cat. No. 377996) was added 1-(4-bromophenyl)acetone (10.0 g, 46.9 mmol, Alfa Aesar, Cat. No. A19028). The reaction mixture was stirred at r.t. under nitrogen overnight. Sodium tetrahydroborate (2.66 g, 70.4 mmol) was added. The mixture was stirred at r.t. for additional 3 h. The reaction mixture was quenched with 2M ammonia in water, and filtered. The solid was washed with AcOEt. The filtrate was concentrated to remove most ethanol, and then was washed with AcOEt twice. The combined organic layers were extracted with 1N HCl aqueous solution (twice). The aqueous HCl solutions were combined, and adjusted with ammonia aqueous solution to pH=10. The result solution was extracted with CH2Cl2. The organic layer was dried with MgSO4, filtered, and concentrated to afford the desired compound which was directly used in the next step reaction without further purification. LCMS (M+H)+: m/z=214.2.

1. stirringThe mixture was stirred at r.t. for additional 3 h
2. customThe reaction mixture was quenched with 2M ammonia in water
3. filtrationfiltered
4. washThe solid was washed with AcOEt
5. concentrationThe filtrate was concentrated
6. customto remove most ethanol
7. washwas washed with AcOEt twice
8. extractionThe combined organic layers were extracted with 1N HCl aqueous solution (twice)
9. extractionThe result solution was extracted with CH2Cl2
10. dry with materialThe organic layer was dried with MgSO4
11. filtrationfiltered
12. concentrationconcentrated