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

HRID 1077190Notes

Reaction equation

HRID 1077190 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C:12]4[CH2:13][CH2:14][C:15](=[O:20])[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:21])[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:21])=[CH:16][C:15](=[O:20])[CH2:14][CH2:13]4)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 1576567313-Ethylgon-5(10)en-3,17-dione

Product 1

HCID 1037926413-Ethylgon-4-ene-3,17-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 13β-ethyl-gon-5(10)-en-3,17-dione (1 g.) with stirring under nitrogen to methanol (25 cc.) containing 11N hydrochloric acid (1.75 cc.) and water (1.1 cc.). Stir for 2 hours, add sodium bicarbonate (1.75 g.) and filter the mixture. Evaporate the filtrate to dryness and recrystallize the residue from ethyl acetate to obtain the title compound; 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

Sources & evidence

ORD record
ord-1c24250cc63146908bdb9eb502b6837d
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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