반응 #159303

반응 방정식

5-hydroxy-2-adamantanone

NaBH4

→

1,4-dihydroxyadamantane

용매

MeOH

HCl

반응 조건

후처리

1. 1
   농축concentrated to dryness
2. 2
   세척washed with water (25 mL) and brine (25 mL)
3. 3
   건조dried over Na2SO4
4. 4
   workup.WAITleft the title compound as a white solid (4.88 g, 94%)
5. 5
   workup.ADDITIONas a 1:1 mixture of cis and trans isomers

실험 절차

A stirred solution of 5-hydroxy-2-adamantanone (5.14 g, 30.9 mmol) in MeOH (100 mL) was cooled in an ice bath and three 1-g NaBH4 caplets (3 g, 78 mmol) were added. The mixture was allowed to warm to rt and stirred overnight. The mixture was diluted with 5% aq HCl (20 mL) and concentrated to dryness. The residue was taken up in EtOAc (200 mL), washed with water (25 mL) and brine (25 mL), and dried over Na2SO4. Removakl of the solvent left the title compound as a white solid (4.88 g, 94%) as a 1:1 mixture of cis and trans isomers.

출처