Реакция #2028900

Уравнение реакции

sodium borohydride

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

→

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

Выход 73.6%

Растворители

ethanol

ethanol

Условия реакции

Обработка

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

Методика

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.

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