Ethanol → HCID 178418380、化合物

HRID 1737928

反応式

HRID 1737928 の反応式
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[CH3:15][N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]2[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[CH3:17].C(O)C.OO>O1CCCC1>[CH3:17][N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C@@H:25]2[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]2)=[CH:21][CH:20]=1)[CH3:15]

参加物

6

反応物 4

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 153795844-{4-[(Dimethylamino)methyl]phenyl}cyclohexan-1-one

生成物 1

HCID 178418380HCID 178418380、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

50 ml (0.05 mol) of a 1 molar solution of lithium tri-sec.-butyl-borohydride in absolute tetrahydrofuran are diluted with 100 ml of absolute tetrahydrofuran under a nitrogen atmosphere and then, at -65° C. to -70° C., with stirring and within 10 minutes, a solution of 5.8 g (0.025 mol) of 4-(4-dimethylaminomethylphenyl)-cyclohexanone in 50 ml of absolute tetrahydrofuran is added thereto. The reaction mixture is then left to react for 3 hours at -70° C. and then heated to ambient temperature within 1 hour. It is then hydrolysed with 20 ml of 75% aqueous ethanol and the organoborane is oxidised with alkaline hydrogen peroxide (10 ml of 6M NaOH/15 ml 30% H2O2). The organic phase is separated off, the aqueous phase is saturated with potassium carbonate and extracted with 50 ml of ethyl acetate. The combined organic extracts are dried with sodium sulphate and evaporated down in vacuo. The greasy residue remaining, which consists of a mixture of cis/trans-4-(4-dimethylaminomethylphenyl)cyclohexanol (trans fraction <5%) is purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1). The product is obtained as a colourless oil. Yield: 4.1 g (71% of theory).

後処理

  1. waitThe reaction mixture is then left
  2. customto react for 3 hours at -70° C.
  3. customThe organic phase is separated off
  4. extractionextracted with 50 ml of ethyl acetate
  5. dry with materialThe combined organic extracts are dried with sodium sulphate
  6. customevaporated down in vacuo
  7. additionwhich consists of a mixture of cis/trans-4-(4-dimethylaminomethylphenyl)cyclohexanol (trans fraction <5%)
  8. customis purified by column chromatography (aluminium oxide neutral, activity stage III, ICN; petroleum ether/methylethyl ketone=5:1)
  9. customThe product is obtained as a colourless oil

出典と根拠

ORDレコード
ord-5d38efe1f6014a85ae5854b9c2a53d28
出典データセット
uspto-grants-1999_10
特許番号
US05962507

関連ノート

読み込み中…