反応 #1065064

反応方程式

4-cyclohexyloxy-2-hydroxybutyl alcohol

benzaldehyde dimethyl acetal

sodium hydrogencarbonate

p-toluenesulfonic acid monohydrate

→

1.3-dioxolane

2-Phenyl-4-(2-cyclohexylethyl)-1,3-dioxolane

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他the reaction
2. 2
   抽出was then extracted with diethyl ether
3. 3
   洗浄The extract was washed with a saturated aqueous solution of sodium chloride
4. 4
   乾燥The organic phase was dried over anhydrous magnesium sulfate
5. 5
   その他the solvent was removed by distillation under reduced pressure
6. 6
   その他The resulting residue was purified by column chromatography through 50 g of silica gel
7. 7
   workup.ADDITIONby volume mixture of diethyl ether and methylene chloride as the eluent

実験手順

43 mg (0.23 mmol) of p-toluenesulfonic acid monohydrate were added, whilst ice-cooling, to a solution of 473 mg (2.51 mmol) of 4-cyclohexyloxy-2-hydroxybutyl alcohol [prepared as described in step above] and 1.14 ml (7.56 mmol) of benzaldehyde dimethyl acetal in 10 ml of methylene chloride, and the resulting mixture was stirred for 2.5 hours at room temperature. In order to stop the reaction, a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture, which was then extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 50 g of silica gel, using a 1:9 by volume mixture of diethyl ether and methylene chloride as the eluent, to give 578 mg (yield 83%) of the title 1.3-dioxolane derivative as an oil.

出典