Reacción #2351

Ecuación de reacción

p-Toluenesulphonyl chloride

tert-butyl (3R)-4-hydroxy-3-methylbutyrate

triethylamine

→

tert-butyl (3R)-3-methyl-4-(p-toluenesulphonyloxy)-butyrate

Rendimiento 96.5%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe mixture was washed in turn with water and with a dilute aqueous sodium carbonate solution
2. 2
   FiltraciónThe organic solution was filtered through phase
3. 3
   Otroseparating paper
4. 4
   Otroevaporated

Procedimiento

p-Toluenesulphonyl chloride (13.2 g) was added portionwise to a stirred mixture of tert-butyl (3R)-4-hydroxy-3-methylbutyrate (11 g), triethylamine (21 ml) and dichloromethane (120 ml) and the mixture was stirred at room temperature for 20 hours. The mixture was washed in turn with water and with a dilute aqueous sodium carbonate solution. The organic solution was filtered through phase separating paper and evaporated to give tert-butyl (3R)-3-methyl-4-(p-toluenesulphonyloxy)-butyrate as an oil (20 g): NMR(CDCl3) δ 7.6(2H,d), 7.33(2H,d), 3.92(2H,d), 2.45(3H,s), 2.18.2.47(2H,m), 2.0-2.15(1H,m), 1.42(9H,s), 0.95(3H,d).

Fuente