Water → 9-Dehydroandrostenedione

HRID 1087671

반응식

HRID 1087671 반응식
O[C@:2]12[CH2:19][CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH2:14][C:15]3=[O:20])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=1.ClS(O)(=O)=O.O>C(Cl)Cl>[CH3:17][C@:16]12[CH2:18][CH:19]=[C:2]3[C@@H:11]([CH2:10][CH2:9][C:8]4[C@:3]3([CH3:22])[CH2:4][CH2:5][C:6](=[O:21])[CH:7]=4)[C@@H:12]1[CH2:13][CH2:14][C:15]2=[O:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 24638Chlorosulfonic acidHCID 104250179alpha-Hydroxyandrost-4-ene-3,17-dione

생성물 1

HCID 2395959-Dehydroandrostenedione

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

9α-Hydroxyandrostenedione (10.00 g.) is dissolved in methylene chloride (100 ml.) and cooled to 0°-5°. Chlorosulfonic acid (5 ml.) is added dropwise and the mixture stirred to 0.5 hour at 0°-5°. Water (50 ml.) is added dropwise while the temperature rises to 23°. The mixture is stirred for 5 minutes and the phases separated. The organic phase is washed with an aqueous sodium bicarbonate solution (10%, 25 ml.) and water (50 ml.) containing 10 ml. of a saturated sodium chloride solution. Each of the aqueous washes is back extracted with the same methylene chloride (25 ml.) which is then added to the organic phase. The organic phase is concentrated to approximately 50 ml. Heptane (100 ml.) is added and the mixture concentrated to approximately 50 ml. with the temperature reaching a maximum of about 35°. The mixture is cooled to 0°-5°, Stirred 0.5 hour, the solids are collected by filtration, under vacuum at 55° to give androsta-4,9(11)-diene-3,17-dione, 8.95 g. (89.5% weight yield, 95.0% chemical yield). GC (Example 1) shows 99% androsta-4,9(11)-diene-3,17-dione.

후처리

  1. temperaturecooled to 0°-5°
  2. customrises to 23°
  3. stirringThe mixture is stirred for 5 minutes
  4. customthe phases separated
  5. washThe organic phase is washed with an aqueous sodium bicarbonate solution (10%, 25 ml.) and water (50 ml.)
  6. additioncontaining 10 ml
  7. extractionEach of the aqueous washes is back extracted with the same methylene chloride (25 ml.) which
  8. additionis then added to the organic phase
  9. concentrationThe organic phase is concentrated to approximately 50 ml
  10. additionHeptane (100 ml.) is added
  11. concentrationthe mixture concentrated to approximately 50 ml
  12. customa maximum of about 35°
  13. temperatureThe mixture is cooled to 0°-5°
  14. stirringStirred 0.5 hour
  15. filtrationthe solids are collected by filtration, under vacuum at 55°

출처 및 근거

ORD 기록
ord-d14822fcf9cf4973aa1bcfea28061c40
출처 데이터셋
uspto-grants-1990_10
특허 번호
USRE033364

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