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Water → HCID 67364108, compound

HRID 1472953
Notes
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Reaction equation

HRID 1472953 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])(OCC)OCC.C(O[C@@H:20]1[C@H:26]2[C@H:27]3[C@H:36]([CH2:37][CH2:38][C@:23]2([CH2:24][CH3:25])[C:22](=[O:40])[CH2:21]1)[C@@H:35]1[C:30](=[CH:31]C(=O)[CH2:33][CH2:34]1)[CH2:29][CH2:28]3)(=O)C1C=CC=CC=1.C(N(CC)CC)C.O>CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:8][C:1]1[CH2:33][CH2:34][C@H:35]2[C:30](=[CH:29][CH2:28][C@@H:27]3[C@@H:36]2[CH2:37][CH2:38][C@@:23]2([CH2:24][CH3:25])[C@H:26]3[CH:20]=[CH:21][C:22]2=[O:40])[CH:31]=1)[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 67361620HCID 67361620, compound

Product 1

HCID 67364108HCID 67364108, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6101
p-Toluenesulfonic acid
Catalyst
HCID 702EthanolSolvent

Procedure

Triethyl orthoformate (0.6 ml, 3.6 mmol) and p-Toluenesulfonic acid (6 mg, 0.032 mmol) were added to a suspension of 15α-benzoyloxy-18-methyl-estr-4-en-3,17-dione (0.6 g, 1.5 mmol) in EtOH (5 ml). The mixture was stirred at room temperature for 1 h. Triethylamine (1 ml, 7.2 mmol) was added, and the mixture was heated under reflux for 30 min, cooled to room temperature and water (50 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 (0.23 g, yield: 50%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperaturecooled to room temperature
  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-c7ba2a54e40243a0ab61c8cb3f762726
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012667B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes