Reaktion #159303

Reaktionsgleichung

5-hydroxy-2-adamantanone

NaBH4

→

1,4-dihydroxyadamantane

Lösungsmittel

MeOH

HCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated to dryness
2. 2
   Waschenwashed with water (25 mL) and brine (25 mL)
3. 3
   Trocknendried 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

Vorschrift

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.

Quelle