Reacción #66675

Ecuación de reacción

2-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene

acetyl chloride

AlCl3

→

1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]-ethanone

Rendimiento 81.9%

Disolventes

DCE

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by H2O (10 ml)
2. 2
   OtroTen minutes after quenching
3. 3
   Extracciónthe aqueous solution was extracted into CH2Cl2
4. 4
   LavadoThe combined extracts was washed with H2O
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated

Procedimiento

To a clear solution of 2-Isopropyl-4-methoxy-1-(toluene-4-sulfonyl)-benzene (5.3 g, 16.56 mmol) in DCE (50 ml) was added acetyl chloride (2.0 g, 24.84 mmol) and AlCl3 (3.3 g, 24.84 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 hrs and quenched by H2O (10 ml). Ten minutes after quenching, the aqueous solution was extracted into CH2Cl2. The combined extracts was washed with H2O, dried over Na2SO4, filtered and concentrated. Flashed chromatography on silica gel (0 to 30% EtOAc in Hex) gave 1-[4-Isopropyl-2-methoxy-5-(toluene-4-sulfonyl)-phenyl]-ethanone (4.7 g, 79%) as white solid.

Fuente