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Diethyl Ether → 13-Ethylgon-4-ene-3,17-dione

HRID 1077191
Notes
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Reaction equation

HRID 1077191 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH:14]=[C:15]([O:20]C)[CH2:16][C:17]=4[CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]12OCC[O:22]1)[CH3:2].C(=O)(O)[O-].[Na+].CCOCC>C(O)(=O)C.O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:22])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 10641203(8'R,9'S,13'S,14'S)-13'-ethyl-3'-methoxyspiro[1,3-dioxolane-2,17'-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]

Product 1

HCID 1037926413-Ethylgon-4-ene-3,17-dioneYield 12%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 962WaterSolvent

Procedure

Heat 13β-ethyl-3-methoxy-17,17-ethylenedioxy-gona-2,5(10)-diene (0.1 g.) in glacial acetic acid (2.5 cc.) and water (1 cc.) on a steam bath for 20 minutes, bring finally to boiling and allow to cool. Add aqueous sodium bicarbonate to neutralize the solution and ether extract the product. Wash, dry and evaporate the ether extracts to furnish a residue (0.065 g.); crystallize from a mixture of acetone and light petroleum to obtain the title compound (0.01 g.), m.p. 154°-5°; ultraviolet absorption peak at 239 mμ (ε15,000); infrared absorption peaks at 5.75, 5.96 μ.

Workup

  1. temperatureto cool
  2. extractionextract the product
  3. washWash
  4. customdry
  5. customevaporate the ether
  6. customto furnish a residue (0.065 g.)
  7. customcrystallize from a mixture of acetone and light petroleum

Sources & evidence

ORD record
ord-42161d2f944e4c54b1c74f44ba7dbc15
Source dataset
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03959322

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes