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Hydrochloric Acid → 13-Ethylgon-4-ene-3,17-dione

HRID 1415008
Notes
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Reaction equation

HRID 1415008 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]2=[O:22])[CH3:2].CO.Cl.C(=O)(O)[O-].[Na+]>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 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 102242MethoxygonadieneHCID 516892Sodium Bicarbonate

Product 1

HCID 1037926413-Ethylgon-4-ene-3,17-dioneYield 81.3%

Reagents, catalysts & solvents 1

HCID 962Water
Solvent

Procedure

Add 13β-ethyl-3-methoxy-gona-2,5(10)-dien-17-one (12.9 g.) with stirring under nitrogen to methanol (300 cc.) containing 11N hydrochloric acid (20 cc) and water (13 cc.). Stir two hours and add sodium bicarbonate (21 g.) portionwise. Filter the mixture and evaporate the filtrate to dryness. Recrystallize the residue from ethyl acetate (75 cc.) to obtain the title compound (10 g.), m.p. 158-161° C; ultraviolet absorption peak at 240 mμ (ε17,800); infrared absorption peaks at 5.78, 6.00, 6.17 μ.

Workup

  1. filtrationFilter the mixture
  2. customevaporate the filtrate to dryness
  3. customRecrystallize the residue from ethyl acetate (75 cc.)

Sources & evidence

ORD record
ord-5a9a8694484c474a9f90165bb63ebbf4
Source dataset
uspto-grants-1977_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04002746

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes