Methyl Ethyl Ketone → Androst-4,7-diene-3,17-dione

HRID 1165509ノート

反応式

HRID 1165509 の反応式
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH:9]=[C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12]([OH:20])[CH2:11]4)[C@@H:6]1[CH2:5][CH2:4][C@@H:3]2[OH:21].CC(=O)CC.CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-]>C1(C)C=CC=CC=1>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C:7](=[CH:8][CH2:9][C:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C:12](=[O:20])[CH:11]=4)[C@@H:6]1[CH2:5][CH2:4][C:3]2=[O:21]

参加物

5

反応物 3

HCID 6569Methyl Ethyl KetoneHCID 11143Aluminum isopropoxideHCID 9817420Androsta-5,7-diene-3b,17b-diol

生成物 1

HCID 14369573Androst-4,7-diene-3,17-dione

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of androst-5,7-diene-3β,17β-diol (2.9 g, 10 mmol) in 150 ml toluene is azeotropically dried for one hour. Butanone (15 ml) is added followed by aluminum isopropoxide (1.7 g,8 mmol) and the mixture is heated at reflux for 2.5 hours. The solution is then concentrated to a volume of 25 ml, diluted with trichloromethane, and washed with 5% hydrochloric acid, aqueous sodium bicarbonate, and brine. Concentration and chromatography affords androst-4,7-diene-3,17-dione.

後処理

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2.5 hours
  3. concentrationThe solution is then concentrated to a volume of 25 ml
  4. additiondiluted with trichloromethane
  5. washwashed with 5% hydrochloric acid, aqueous sodium bicarbonate, and brine
  6. concentrationConcentration and chromatography

出典と根拠

ORDレコード
ord-3ab383a8e0344875ba135a2c5ef4f68c
出典データセット
uspto-grants-1990_03
特許番号
US04910226

反応ノート

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