Ethanol → HCID 69790149, compound

HRID 1815783Notes

Reaction equation

HRID 1815783 reaction equation
[CH:1]([C@@H:3]1[CH2:20][C:19]2[CH:18]=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:23])[CH2:7][CH:6]=1)=[CH2:2].C(O)C.O>O1CCCC1>[CH:1]([C@@H:3]1[CH2:20][C:19]2[CH:18]=[C:17]([O:21][CH3:22])[CH:16]=[CH:15][C:14]=2[C@@H:13]2[C@@H:4]1[C:5]1[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C@@H:8]([OH:23])[CH2:7][CH:6]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 962Water2×HCID 69789601HCID 69789601, compound

Product 1

HCID 69790149HCID 69790149, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

—Sodium borohydride (8.54 g) was added to a solution of (7α)-7-ethenyl-3-methoxyestra-1,3,5(10),14-tetraen-17-one (8.72 g) in a mixture of tetrahydrofuran (161 ml), ethanol (161 ml), and water (26.4 ml). The reaction mixture was stirred at room temperature for 50 min. and then poured into water. The product was extracted into ethyl acetate; the combined organic phases were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,17β)-7-ethenyl-3-methoxyestra-1,3,5(10),14-tetraen-17-ol (8.45 g).

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washthe combined organic phases were washed with water
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and brine, dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08213aa6d12240d39e7267395f5d1fab
Source dataset
uspto-grants-2005_04
Patent number
US06881728B1

Reaction notes

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