Reacción #335015

Ecuación de reacción

acetoxyacetyl chloride

2,6-diisopropylaniline

triethylamine

→

brown solid

Rendimiento 40.2%

N-[2,6-Bis(1-methylethyl)phenyl]-2-acetoxy Acetamide

Rendimiento 40.2%

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   FiltraciónThe mixture is filtered through a small pad of silica gel
3. 3
   ConcentraciónThe filtrate is concentrated

Procedimiento

To a solution of acetoxyacetyl chloride (13.5 g, 98.7 mmol) in toluene (70 mL) at 0° C. is added dropwise via a dropping funnel a solution of 2,6-diisopropylaniline (17.5 g, 98.7 mmol) and triethylamine (20.6 mL, 148.1 mmol) in toluene (20 mL). After completion of the addition, the mixture is allowed to warm to room temperature and stirred for 24 hours. The mixture is filtered through a small pad of silica gel. The filtrate is concentrated to afford 11 g of a brown solid. The precipitate is suspended in ethyl acetate and stirred overnight. After filtration, the filtrate is concentrated to give another 10 g of a brown solid. Recrystallization (ethyl acetate/hexane) of the combined material provided 12 g of the title compound as an off-white solid; mp 179°-182° C.

Fuente