Water → HCID 67362260, compound

HRID 1472958Notes

Reaction equation

HRID 1472958 reaction equation
C(N(CC)CC)C.C(O[C@@H:12]1[C@H:18]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:15]2([CH2:16][CH3:17])[C:14](=[O:32])[CH2:13]1)[C@@H:27]1[C:22](=[CH:23][C:24](=[O:31])[CH2:25][CH2:26]1)[CH2:21][CH2:20]3)(=O)C.O>CCO>[CH3:17][CH2:16][C@:15]12[CH2:30][CH2:29][C@H:28]3[C@@H:19]([CH2:20][CH2:21][C:22]4[C@@H:27]3[CH2:26][CH2:25][C:24](=[O:31])[CH:23]=4)[C@@H:18]1[CH:12]=[CH:13][C:14]2=[O:32]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 67361589HCID 67361589, compound

Product 1

HCID 67362260HCID 67362260, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (4 ml, 28.7 mmol) was added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (4 g, 11.6 mmol) in EtOH (24 ml). The mixture was heated under reflux for 2 h. It was cooled to room temperature and water (50 ml) was added. The precipitate was filtered, washed with a 6/4 EtOH/water solution and dried under vacuum. The residue was purified by flash chromatography on silica gel to afford 18-methyl-estra-4,15-dien-3,17-dione (2 g, yield: 62%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. filtrationThe precipitate was filtered
  4. washwashed with a 6/4 EtOH/water solution
  5. customdried under vacuum
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0bd93415cadc4004bf89607adc57d30e
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

Loading…