Réaction #2328978

Équation de réaction

sodium borohydride

THF

( 3-3 )

4′-vinylbicyclohexyl-4-carbaldehyde

ammonium chloride

→

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

Solvants

ethanol

ethyl acetate

water

Conditions de réaction

Traitement

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

Mode opératoire

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