Reaction #2328978

Reaction equation

sodium borohydride

THF

( 3-3 )

4′-vinylbicyclohexyl-4-carbaldehyde

ammonium chloride

→

trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethanol

Solvents

ethanol

ethyl acetate

water

Conditions

Workup

1. 1
   workup.STIRRINGwhile stirring the inner temperature
2. 2
   TemperatureAfter raising the temperature to room temperature
3. 3
   workup.STIRRINGstirring for 2 hours
4. 4
   Otherterminating
5. 5
   Otherthe reaction
6. 6
   workup.ADDITIONThe saturated saline was added to the reacted solution
7. 7
   Otherthe organic layer was separated
8. 8
   Extractionthe aqueous layer was extracted with ethyl acetate (twice)
9. 9
   WashThe combined organic layer was washed with saturated saline
10. 10
    Dryingdried over anhydrous magnesium sulfate
11. 11
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
12. 12
    Otherthe residue was purified by column chromatography

Procedure

A THF (180 mL) solution of 60.1 g of a nearly colorless solid obtained in (3-3) was added dropwise in an ethanol (120 mL) solution of 1.65 g of sodium borohydride under stirring at −10° C. while stirring the inner temperature. After raising the temperature to room temperature and stirring for 2 hours, water, ethyl acetate and an aqueous ammonium chloride aqueous were added, thereby terminating the reaction. The saturated saline was added to the reacted solution, and the organic layer was separated, and then the aqueous layer was extracted with ethyl acetate (twice). The combined organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography to obtain 15.4 g of trans-4-(trans-4-vinylcyclohexyl)cyclohexylmethanol as a white solid.

Source