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

HRID 371815

Reaction equation

HRID 371815 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. 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-375ad16dbc2f48c98abcf840ec02c66b
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Linked notes

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