Reacción #595332

Ecuación de reacción

water

potassium carbonate

(S)-(−)-3-chloro-1,2-propanediol acetonide

4-hydroxybenzaldehyde

→

4-{[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]methoxy}benzaldehyde

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture is extracted three times with in each case 500 ml of ethyl acetate
2. 2
   LavadoThe combined organic phases are washed in each case once with 500 ml water and 500 ml of sat. aqueous sodium chloride solution
3. 3
   SecadoAfter drying over magnesium sulfate
4. 4
   Otrothe solvent is removed on a rotary evaporator
5. 5
   Otrothe residue is purified by column chromatography on silica gel 60 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8)

Procedimiento

31.2 g (255.4 mmol) of 4-hydroxybenzaldehyde are initially charged in 400 ml of dry DMF, and 105.7 g (766.1 mmol) of potassium carbonate and 50.0 g (332.0 mmol) of (S)-(−)-3-chloro-1,2-propanediol acetonide are added at RT. The mixture is stirred at 160° C. for 16 h. 4000 ml of water are then added, and the mixture is extracted three times with in each case 500 ml of ethyl acetate. The combined organic phases are washed in each case once with 500 ml water and 500 ml of sat. aqueous sodium chloride solution. After drying over magnesium sulfate, the solvent is removed on a rotary evaporator and the residue is purified by column chromatography on silica gel 60 (mobile phase gradient: ethyl acetate/petroleum ether 1:9→2:8).

Fuente