Reacción #50896

Ecuación de reacción

phenylacetyl chloride

2-trichloroacetyl pyrrole

aluminum trichloride

→

2,2,2-Trichloro-1-(4-phenylacetyl-1H-pyrrol-2-yl)-ethanone

Rendimiento 60.0%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoGradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield
2. 2
   Otroprovided a retention time of 4.9 minutes

Procedimiento

In a dry flask, phenylacetyl chloride (1 equivalent) was combined with 2-trichloroacetyl pyrrole (1 equivalent) in a minimum amount of dichloromethane (DCM). To the resulting solution, at ambient temperature, was added aluminum trichloride (1 equivalent). After 2 hours, the reaction mixture was applied directly onto a silica gel column. Gradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 1 in 60% yield. 1H NMR (CDCl3) □4.0 (s, 2H), 7.1-7.35 (m, 7H), 9.7 (br s, NH). HPLC using method B (as described below for Example 5) provided a retention time of 4.9 minutes. LC/MS (M+1) 330.2, (M−1) 328.1.

Fuente