Ethanol → HCID 69790149, compound

HRID 427762Notes

Reaction equation

HRID 427762 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>[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

4

Reactant 2

HCID 702EthanolHCID 69789601HCID 69789601, compound

Product 1

HCID 69790149HCID 69790149, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

—Sodium borohydride (1.47 g) was added to a solution of (7α)-7-ethenyl-3-methoxyestra-1,3,5(10),14-tetraen-17-one (1.50 g) obtained in the previous step in a mixture of tetrahydrofliran (27.8 ml), ethanol (27.8 ml) and water (4.55 ml). The reaction mixture was stirred for 50 min. and then poured into water. The product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated, to afford (7α,17β)-7-ethenyl-3-methoxyestra-1,3,5(10),14-tetraen-17-ol (1.47 g). The product was used in the following step without fiLrther purification.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6af34a87c81431b9b965e873c58fd17
Source dataset
uspto-grants-2001_11
Patent number
US06313108B1

Reaction notes

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