Water → HCID 70046675, compound

HRID 233641Notes

Reaction equation

HRID 233641 reaction equation
[C:1]([CH:6]=[CH:7][CH2:8][O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@:16]3([OH:34])[CH2:17][CH2:18][C@@H:19]2[C:29]2[CH:33]=[CH:32][O:31][CH:30]=2)[CH2:11]1)(OCC)=[O:2].O>O1CCCC1.[H-].COCCO[Al+]OCCOC.[Na+].[H-]>[OH:2][CH2:1][CH2:6][CH2:7][CH2:8][O:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@:16]3([OH:34])[CH2:17][CH2:18][C@@H:19]2[C:29]2[CH:33]=[CH:32][O:31][CH:30]=2)[CH2:11]1

Participants

5

Reactant 2

HCID 962WaterHCID 70046069HCID 70046069, compound

Product 1

HCID 70046675HCID 70046675, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideSolvent

Procedure

To a solution of 0.40 g of 3β-(3-carbethoxyprop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol in 30 ml of anhydrous tetrahydrofuran, 2 ml of sodium bis(2-methoxyethoxy)aluminum hydride (solution 3.4M in toluene) were added at room temperature. The solution was kept at reflux temperature for 8 hrs, then 10 ml of water were added and the organic solution was evaporated to dryness under reduced pressure. The residue was extracted with ethyl acetate and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography using n-hexane/ethyl acetate 70/30 as eluant to give 0.30 g of 3β-(4-hydroxybutoxy)-17β-(3-furyl)-5β-androstan-14β-ol, as a white pasty solid.

Workup

  1. temperatureat reflux temperature for 8 hrs
  2. customthe organic solution was evaporated to dryness under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude product was purified by flash-chromatography

Sources & evidence

ORD record
ord-ed41e9a71f4542799034bed3d12bf60d
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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