Water → HCID 67364108, compound

HRID 1472951Notes

Reaction equation

HRID 1472951 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(NC(C)C)(C)C.O>CCO.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 4

HCID 962WaterHCID 7912DiisopropylamineHCID 31214Ethyl orthoformateHCID 67361589HCID 67361589, compound

Product 1

HCID 67364108HCID 67364108, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

Triethyl orthoformate (5 ml, 30 mmol) and p-Toluenesulfonic acid (50 mg, 0.26 mmol) were added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (5 g, 14.5 mmol) in EtOH (30 ml). The mixture was stirred at room temperature for 1 h. Diisopropylamine (6.3 ml, 36 mmol) was added, and the mixture was heated under reflux for 2 h, cooled to 10° C. and water (15 ml) was then added. The precipitate was filtered, washed with water and dried. The crude product was purified by flash chromatography, eluting with heptane and ethyl acetate (7:3), crystallized from heptane, and dried under vacuum to afford 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one (3.18 g, yield: 71%).

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
  7. customThe crude product was purified by flash chromatography
  8. washeluting with heptane and ethyl acetate (7:3)
  9. customcrystallized from heptane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-821089dbabf44f3a8cbd405b73e95498
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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