Reacción #53261

Ecuación de reacción

p-toluenesulfonic acid

methanol

isopropyl ether

water

→

benzyl 6-methyl-3-hydroxyheptanoate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturaunder reflux for one hour
3. 3
   OtroThe organic layer was separated
4. 4
   Extracciónthe aqueous layer was extracted with isopropyl ether
5. 5
   Lavadowashed with water
6. 6
   Secadoa saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
7. 7
   OtroAfter the solvent was removed in vacuo under reduced pressure
8. 8
   Otrothe residue was purified by a silica gel column chromatography (silica gel 70 g, hexane: ethyl acetate=100:15)

Procedimiento

To a solution of the benzyl ester (3.11 g) obtained in Synthesis Example 80 in methanol (70 ml) was added p-toluenesulfonic acid (0.35 g) and the mixture was heated under reflux for one hour. After cooling to room temperature, isopropyl ether and water were added thereto. The organic layer was separated and the aqueous layer was extracted with isopropyl ether. The extract was combined with the organic layer and washed with water, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo under reduced pressure, the residue was purified by a silica gel column chromatography (silica gel 70 g, hexane: ethyl acetate=100:15) to afford 1.38 g of benzyl 6-methyl-3-hydroxyheptanoate.

Fuente