반응 #2328978

반응 방정식

sodium borohydride

THF

( 3-3 )

4′-vinylbicyclohexyl-4-carbaldehyde

ammonium chloride

→

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

용매

ethanol

ethyl acetate

water

반응 조건

후처리

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

실험 절차

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.

출처