Potassium Carbonate → HCID 67362893, compound

HRID 1472956Notes

Reaction equation

HRID 1472956 reaction equation
C(O[C@@H:5]1[C@H:11]2[C@H:12]3[C@H:21]([CH2:22][CH2:23][C@:8]2([CH2:9][CH3:10])[C:7](=[O:26])[CH2:6]1)[C@@H:20]1[C:15]([CH:16]=[C:17]([O:24][CH3:25])[CH2:18][CH2:19]1)=[CH:14][CH2:13]3)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:25][O:24][C:17]1[CH2:18][CH2:19][C@H:20]2[C:15](=[CH:14][CH2:13][C@@H:12]3[C@@H:21]2[CH2:22][CH2:23][C@@:8]2([CH2:9][CH3:10])[C@H:11]3[CH:5]=[CH:6][C:7]2=[O:26])[CH:16]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67362263HCID 67362263, compound

Product 1

HCID 67362893HCID 67362893, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of 15α-acetoxy-3-methoxy-18-methyl-estra-3,5-dien-17-one (1 g, 2.8 mmol) in suspension in a 1/1 MeOH/water solution (20 ml), and potassium carbonate (1 g, 7.23 mmol) was heated at 50° C. for 1 h. The mixture was allowed to cool to room temperature and the precipitate was filtered, washed with water and dried under vacuum to afford 3-methoxy-18-methyl-estra-3,5,15-trien-17-one (0.67 g, yield: 80%). mp: 159-161° C.; 1H-NMR δ=0.72 (t, 3H), 0.9-2.4 (m, 16H), 3.55 (s, 3H), 5.18 (s, 1H), 5.28 (d, 1H), 5.95 (m, 1H), 7.45 (d, 1H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2c5789426a7248ac87f5adf5c2eac355
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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