Allyl bromide → HCID 22854038, compound

HRID 725263Notes

Reaction equation

HRID 725263 reaction equation
[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][C@H:12](O)[CH2:11]4)[C@@:6]1([OH:21])[CH2:5][CH2:4][CH2:3]2.[H-].[Na+].C(Br)C=C>O1CCCC1>[CH3:1][C@:2]12[CH2:19][CH2:18][C@H:17]3[C@@H:7]([CH2:8][CH2:9][C@H:10]4[C@:15]3([CH3:16])[CH2:14][CH2:13][CH2:12][CH2:11]4)[C@@:6]1([OH:21])[CH2:5][CH2:4][CH2:3]2

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 13654053HCID 13654053, compound

Product 1

HCID 22854038HCID 22854038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6.05 g of 17β-12-(1,3-dioxolanyl)]-5β-androstan-3β,14β-diol in 80 ml of dry tetrahydrofuran. 5.80 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. Alter cooling. 18.0 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. The residue was purified by flash-chromatography using n-hexane/ethyl acetate 80/20 as the eluant to give 5.20 g of 3β-prop-(2-en)oxy-17β-(1,3-dioxolanyl)]-5β-androstan-14β-ol as a white solid.

Workup

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

Sources & evidence

ORD record
ord-101c7ad61fff41b6a0475424cea7d474
Source dataset
uspto-grants-1998_01
Patent number
US05705662

Reaction notes

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