反応 #53261

反応方程式

p-toluenesulfonic acid

methanol

isopropyl ether

water

→

benzyl 6-methyl-3-hydroxyheptanoate

反応条件

後処理

1. 1
   温度the mixture was heated
2. 2
   温度under reflux for one hour
3. 3
   その他The organic layer was separated
4. 4
   抽出the aqueous layer was extracted with isopropyl ether
5. 5
   洗浄washed with water
6. 6
   乾燥a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
7. 7
   その他After the solvent was removed in vacuo under reduced pressure
8. 8
   その他the residue was purified by a silica gel column chromatography (silica gel 70 g, hexane: ethyl acetate=100:15)

実験手順

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.

出典