反応 #1742

反応方程式

4-(4-dimethylaminomethylphenyl)-cyclohexanone

sodium borohydride

→

trans-4-(4-Dimethylaminomethylphenyl)-cyclohexanol

溶媒

methanol

反応条件

後処理

1. 1
   その他to react for 1.5 hours at ambient temperature
2. 2
   その他evaporated down in vacuo
3. 3
   workup.ADDITIONThe residue remaining is mixed with water
4. 4
   workup.STIRRINGstirred for 30 minutes at ambient temperature
5. 5
   抽出extracted several times with chloroform
6. 6
   乾燥The combined extracts are dried with sodium sulphate
7. 7
   その他evaporated down in vacuo
8. 8
   workup.ADDITIONwhich consists of a mixture of trans/cis-4-(4-dimethylaminomethyl-phenyl)-cyclohexanol (cis fraction <10%)
9. 9
   その他is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1)
10. 10
    その他White crystals are obtained

実験手順

To a solution of 11.1 g (0.048 mol) of 4-(4-dimethylaminomethylphenyl)-cyclohexanone in 100 ml of absolute methanol, which has been cooled to -10° C., is added 1.82 g (0.048 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 1.5 hours at ambient temperature and then evaporated down in vacuo. The residue remaining is mixed with water, acidified with concentrated hydrochloric acid, stirred for 30 minutes at ambient temperature, made alkaline with 50% sodium hydroxide solution and extracted several times with chloroform. The combined extracts are dried with sodium sulphate and evaporated down in vacuo. The residue remaining, which consists of a mixture of trans/cis-4-(4-dimethylaminomethyl-phenyl)-cyclohexanol (cis fraction <10%) is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1). White crystals are obtained, melting point 63°-65° C.

出典