반응 #2028900

반응 방정식

sodium borohydride

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

→

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

수율 73.6%

용매

ethanol

ethanol

반응 조건

후처리

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

실험 절차

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.

출처