Cholesterol → 1,4,6-Cholestatrien-3-one

HRID 651943

反応式

HRID 651943 の反応式
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3]>O1CCOCC1>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16](=[CH:17][C:18](=[O:19])[CH:20]=[CH:21]2)[CH:15]=[CH:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

参加物

3

反応物 1

HCID 5997Cholesterol

生成物 1

HCID 1073901,4,6-Cholestatrien-3-one収率 60.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Cholesterol (19.3 gms) and dichlorodicyanoquinone (38 gms) in dry dioxan (500 ml) were heated under reflux for 22 hrs. The mixture was then cooled, filtered and the filtrate evaporated to dryness. Chromatography of the residue on alumina and elution with benzene/hexane followed by elution with benzene afforded the trienone as a pale oil (11.5 gms) which solidified on standing. Physical properties of this material were appropriate.

後処理

  1. temperatureunder reflux for 22 hrs
  2. temperatureThe mixture was then cooled
  3. filtrationfiltered
  4. customthe filtrate evaporated to dryness
  5. washChromatography of the residue on alumina and elution with benzene/hexane
  6. washfollowed by elution with benzene

出典と根拠

ORDレコード
ord-b8b7c550be1944b7b8496543f44a2355
出典データセット
uspto-grants-1987_06
特許番号
US04670190

関連ノート

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