反応 #2028900

反応方程式

sodium borohydride

3-oxo-3-(trans-4-propyl-cyclohexyl)-propionic acid ethyl ester

→

1-(trans-4-propyl-cyclohexyl)-propane-1,3-diol

収率 73.6%

溶媒

ethanol

ethanol

反応条件

後処理

1. 1
   その他The reaction mixture was quenched with water (1,000 ml), to which ethyl acetate (500 ml)
2. 2
   workup.ADDITIONwas added
3. 3
   その他to give two layers The water layer
4. 4
   抽出was extracted with ethyl acetate (500 ml) twice
5. 5
   洗浄the combined organic layer was washed with water
6. 6
   乾燥dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   その他The residue was purified by silica gel chromatography (silica gel: 500 g, eluent: heptane/ethyl acetate=50/50 by volume)

実験手順

An ethanol (300 ml) solution of (3-oxo-3-(trans-4-propyl-cyclohexyl)-propionic acid ethyl ester (3) (220.0 g) prepared in the second step was added dropwise at 50° C. or lower to a suspension of sodium borohydride (45 g) in ethanol (500 ml), in a reaction vessel under an atmosphere of nitrogen, and the stirring was continued at room temperature for 5 hours. The reaction mixture was quenched with water (1,000 ml), to which ethyl acetate (500 ml) was added to give two layers The water layer was extracted with ethyl acetate (500 ml) twice, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 500 g, eluent: heptane/ethyl acetate=50/50 by volume) to give 1-(trans-4-propyl-cyclohexyl)-propane-1,3-diol (4) (135 g) in 67% yield.

出典