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

HRID 233639Notes

Reaction equation

HRID 233639 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a155f1cd7c4346c6a63649a36dcdae14
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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