25-Hydroxycholesterol → 25-Hydroxycholesta-1,4,6-trien-3-one

HRID 651947

反応式

HRID 651947 の反応式
[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:4])[CH3:3]>O1CCOCC1>[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17](=[CH:18][C:19](=[O:20])[CH:21]=[CH:22]2)[CH:16]=[CH:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:3])[CH3:4]

参加物

3

反応物 1

HCID 6509425-Hydroxycholesterol

生成物 1

HCID 2279738725-Hydroxycholesta-1,4,6-trien-3-one

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

25-Hydroxycholesterol (3.4 gms) and dichlorodicyanoquinone (6.5 gms) dissolved in purified dioxan (100 mls) were heated at reflux for 20 hrs. The mixture was filtered and the solvent evaporated. Chromatography of the residue on alumina and elution with ethyl acetate and benzene afforded the trienone. Recrystallization from methanol gave the title compound, melting point 183°-184°. νmax. 3600, 1650 and 1600 cm-1.

後処理

  1. temperaturewere heated
  2. temperatureat reflux for 20 hrs
  3. filtrationThe mixture was filtered
  4. customthe solvent evaporated
  5. washChromatography of the residue on alumina and elution with ethyl acetate and benzene
  6. customafforded the trienone
  7. customRecrystallization from methanol

出典と根拠

ORDレコード
ord-3c2068ef9cc742e1ade3feaa90bafb20
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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