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

HRID 1165509노트

반응식

HRID 1165509 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3ab383a8e0344875ba135a2c5ef4f68c
출처 데이터셋
uspto-grants-1990_03
특허 번호
US04910226

반응 노트

불러오는 중…