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

HRID 1733073Notes

Reaction equation

HRID 1733073 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-f64047b1c3954485b768fb2a20273842
Source dataset
uspto-grants-1980_12
Patent number
US04239681

Reaction notes

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