Potassium Carbonate → HCID 67364108, compound

HRID 1472966Notes

Reaction equation

HRID 1472966 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])(OCC)OCC.C(O[C@@H:15]1[C@H:21]2[C@H:22]3[C@H:31]([CH2:32][CH2:33][C@:18]2([CH2:19][CH3:20])[C:17](=[O:35])[CH2:16]1)[C@@H:30]1[C:25](=[CH:26]C(=O)[CH2:28][CH2:29]1)[CH2:24][CH2:23]3)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:8][C:1]1[CH2:28][CH2:29][C@H:30]2[C:25](=[CH:24][CH2:23][C@@H:22]3[C@@H:31]2[CH2:32][CH2:33][C@@:18]2([CH2:19][CH3:20])[C@H:21]3[CH:15]=[CH:16][C:17]2=[O:35])[CH:26]=1)[CH3:10]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 31214Ethyl orthoformateHCID 67361589HCID 67361589, compound

Product 1

HCID 67364108HCID 67364108, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Triethyl orthoformate (2 ml, 12 mmol) and p-Toluenesulfonic acid (20 mg, 0.10 mmol) were added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (2 g, 5.81 mmol) in ethanol (20 ml). The mixture was stirred at room temperature for 1 h. Potassium carbonate (1.1 g, 8.06 mmol) in solution in water (20 ml) was added and the mixture was heated under reflux for 2 h, cooled to 10° C. and water (20 ml) was then added. The precipitate was filtered, washed with water and dried under vacuum, to afford 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one (1.3 g, yield: 78%). mp and 1H-NMR were in accordance with those obtained for example 2. HPLC analysis was as shown in FIG. 1b.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled to 10° C.
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4923c750e02747e496387192df33c89a
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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