Water → HCID 67364108, compound

HRID 1472949Notes

Reaction equation

HRID 1472949 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(N(CC)CC)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 8471TriethylamineHCID 31214Ethyl orthoformateHCID 67361589HCID 67361589, compound

Product 1

HCID 67364108HCID 67364108, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 702EthanolSolvent

Procedure

Triethyl orthoformate (5 ml, 30 mmol) and p-Toluenesulfonic acid (25 mg, 0.13 mmol) were added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (5 g, 14.5 mmol) in EtOH (40 ml). The mixture was stirred at room temperature for 1 h. Triethylamine (5 ml, 35.9 mmol) was added, and the mixture was heated under reflux for 1 h, cooled to room temperature and water (30 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 (4 g, yield: 88%).

Workup

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

Sources & evidence

ORD record
ord-09a6441d204449bb9e84d0a7269dbfa6
Source dataset
uspto-grants-2015_04
Patent number
US09012667B2

Reaction notes

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