Water → 19-Methoxyandrost-4-ene-3,17-dione

HRID 1390759Notes

Reaction equation

HRID 1390759 reaction equation
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.F[B-](F)(F)F.[CH3:28][O+](C)C.O>C(Cl)Cl>[CH3:28][O:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2

Participants

5

Reactant 3

HCID 962WaterHCID 25237919-HydroxyandrostenedioneHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 5415304219-Methoxyandrost-4-ene-3,17-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19-Hydroxyandrost-4-ene-3,17-dione is dissolved in methylenechloride and trimethyloxonium fluoroborate added thereto. After stirring at room temperature for a period of two hours, water is added to the reaction mixture, the organic layer is separated, dried over magnesium sulfate and the solvent removed under vacuum. The residue is crystallized from an acetone-hexane solution to yield the desired 19-methoxyandrost-4-ene-3,17-dione.

Workup

  1. customthe organic layer is separated
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent removed under vacuum
  4. customThe residue is crystallized from an acetone-hexane solution

Sources & evidence

ORD record
ord-988be6b66f074c808c733a419c54a46e
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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