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

HRID 861810

反応式

HRID 861810 の反応式
[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]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 11143Aluminum isopropoxideHCID 4394237-Dehydrocholesterol

生成物 1

HCID 15480063Cholesta-5,7-diene-3-one収率 103.1%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c3d7d2edf9a4f2e830ee5a7679efc00
出典データセット
uspto-grants-1998_02
特許番号
US05716777

関連ノート

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