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

HRID 651947

반응식

HRID 651947 반응식
[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]

참가 물질

3

반응물 1

HCID 6509425-Hydroxycholesterol

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3c2068ef9cc742e1ade3feaa90bafb20
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670190

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