반응 #2320112

반응 방정식

5-Bromo-2-chlorobenzotrifluoride

1-benzyl-4-piperidone

→

title compound

수율 64.0%

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

수율 64.0%

용매

diethyl ether

diethyl ether

diethyl ether

반응 조건

후처리

1. 1
   기타The reaction gave rise to a solution of Grignard's reagent
2. 2
   기타finally quenched with saturated ammonium chloride solution (40 ml)
3. 3
   추출The mixture was extracted several times with EtOAc
4. 4
   건조the combined organic phases were dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타evaporated to dryness

실험 절차

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).

출처