Reaction #2028900

Reaction equation

sodium borohydride

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

→

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

Yield 73.6%

Solvents

ethanol

ethanol

Conditions

Workup

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

Procedure

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.

Source