反应 #2320112

反应方程式

5-Bromo-2-chlorobenzotrifluoride

1-benzyl-4-piperidone

→

title compound

收率 64.0%

1-Benzyl-4-(4-chloro-3-trifluoromethyl-phenyl)-piperidine-4-ol

收率 64.0%

溶剂

diethyl ether

diethyl ether

diethyl ether

反应条件

后处理

1. 1
   其他The reaction gave rise to a solution of Grignard's reagent
2. 2
   其他finally quenched with saturated ammonium chloride solution (40 ml)
3. 3
   萃取The mixture was extracted several times with EtOAc
4. 4
   干燥the combined organic phases were dried (MgSO4)
5. 5
   过滤filtered
6. 6
   其他evaporated to dryness

实验过程

A solution of 5-Bromo-2-chlorobenzotrifluoride (5 g, 19.2 mmol) in dry diethyl ether (40 ml) was added dropwise at room temperature to a mixture of Mg (470 mg) in dry diethyl ether (20 ml) under a stream of Argon (g). The reaction gave rise to a solution of Grignard's reagent. A solution of 1-benzyl-4-piperidone (1.3 g, 6.88 mmol) in dry diethyl ether (30 ml) was added dropwise via syringe at room temperature. The combined mixture was stirred for 1 hour, and finally quenched with saturated ammonium chloride solution (40 ml). The mixture was extracted several times with EtOAc and the combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The oily residue was chromathographed on a silica column using EtOAc:toluene (1:1 (v/v)) as eluent affording the title compound (1.6 g, 64%). MS m/z (relative intensity, 70 eV) 369 (M+, 23), 278 (15), 91 (bp), 65 (16), 56 (21).

来源