Hydrochloric Acid → Cholesta-5,7-diene-3-one

HRID 861810

반응식

HRID 861810 반응식
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C:20]4=[CH:19][CH:18]=[C:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].Cl>CC(=O)CC>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:28])[C@H:12]([C:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:27])[C:20]([CH2:25][C:24](=[O:26])[CH2:23][CH2:22]2)=[CH:19][CH:18]=3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 4394237-Dehydrocholesterol

생성물 1

HCID 15480063Cholesta-5,7-diene-3-one수율 103.1%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

1.15 g of dehydrocholesterol was dissolved in 15 ml of 2-butanone, 0.34 g of aluminum isopropoxide was added, and the mixture was heated at reflux temperature for 75 mutes. After cooling on an ice bath, 15 ml of 2N hydrochloric acid was added, the phases were separated, and the organic phase was washed twice with 7.5 ml of 2N hydrochloric acid. The aqueous phase was extracted with toluene, and the combined organic phases were washed with water and brine, dried, and evaporated to yield 1.18 g of crude cholesta-5,7-diene-3-one as a viscous oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 75 mutes
  3. temperatureAfter cooling on an ice bath
  4. customthe phases were separated
  5. washthe organic phase was washed twice with 7.5 ml of 2N hydrochloric acid
  6. extractionThe aqueous phase was extracted with toluene
  7. washthe combined organic phases were washed with water and brine
  8. customdried
  9. customevaporated

출처 및 근거

ORD 기록
ord-9c3d7d2edf9a4f2e830ee5a7679efc00
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716777

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