Allyl bromide → 3beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-ol

HRID 233639노트

반응식

HRID 233639 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C@H:6]2[CH2:11][CH2:10][C@:9]3([OH:26])[C@H:12]4[C@H:22]([CH2:23][CH2:24][C@:7]23[CH3:8])[C@:20]2([CH3:21])[C@@H:15]([CH2:16][C@@H:17]([OH:25])[CH2:18][CH2:19]2)[CH2:14][CH2:13]4)=[CH:2]1.[H-].[Na+].[CH2:29](Br)[CH:30]=[CH2:31]>O1CCCC1>[CH2:31]([O:25][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@H:15]([CH2:14][CH2:13][C@@H:12]3[C@@H:22]2[CH2:23][CH2:24][C@@:7]2([CH3:8])[C@:9]3([OH:26])[CH2:10][CH2:11][C@@H:6]2[C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)[CH2:16]1)[CH:30]=[CH2:29]

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 1606964617beta-(3-Furyl)-5beta,14beta-androstane-3beta,14beta-diol

생성물 1

HCID 228545783beta-Prop-2-enoxy-17beta(3-furyl)-5beta-androstan-14beta-ol수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.60 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc.(C), 1966, 377) in 50 ml of dry tetrahydrofuran, 0.44 g of sodium hydride (60% dispersion in mineral oil) were added under nitrogen atmosphere at room temperature and the resulting mixture was stirred at reflux temperature for 6 hrs; 1.4 g of allyl bromide were added and the reflux continued for further 20 hrs. The mixture was quenched with water and the organic solvent was distilled under reduced pressure. The residue was extracted with ethyl acetate, the organic solution was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 80/20 as eluant to give 0.58 g of 3β-(prop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

후처리

  1. temperatureat reflux temperature for 6 hrs
  2. customThe mixture was quenched with water
  3. distillationthe organic solvent was distilled under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. dry with materialthe organic solution was dried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was purified by flash-chromatography (SiO2)

출처 및 근거

ORD 기록
ord-a155f1cd7c4346c6a63649a36dcdae14
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593982

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