Hydrochloric Acid → 13-Ethyl-17beta-hydroxy-6alpha-methylgon-4-en-3-one

HRID 1077224Notes

Reaction equation

HRID 1077224 reaction equation
C[O:2][C:3]1[CH2:4][C:5]2[CH:6]([CH3:23])[CH2:7][C@H:8]3[C@H:16]4[C@@:12]([CH2:18][CH3:19])([C@@H:13]([OH:17])[CH2:14][CH2:15]4)[CH2:11][CH2:10][C@@H:9]3[C:20]=2[CH2:21][CH:22]=1.Cl.O>CO.[Cl-].[Na+].O>[CH2:18]([C@:12]12[CH2:11][CH2:10][C@@H:9]3[C@@H:20]4[C:5]([C@@H:6]([CH3:23])[CH2:7][C@H:8]3[C@@H:16]1[CH2:15][CH2:14][C@@H:13]2[OH:17])=[CH:4][C:3](=[O:2])[CH2:22][CH2:21]4)[CH3:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68144451HCID 68144451, compound

Product 1

HCID 6814454813-Ethyl-17beta-hydroxy-6alpha-methylgon-4-en-3-oneYield 31.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Stir dl-3-methoxy-17β-hydroxy-6-methyl-13-ethylgona-2,5(10)-diene (1.0 g) in methanol (54 cc) containing concentrated hydrochloric acid (3.6 cc) and water (2.4 cc) under nitrogen for 1.5 hours. Pour into brine, extract with ether and isolate the crude product. Chromatograph on Grade I neutral alumina (50 g) and recrystallize from ether-hexane to obtain the title compound (0.30 g), m.p. 127°-130°, λ max. KBr 2.98 μ, 6.03 μ; λ max. EtOH 240 mμ (ε16,500).

Workup

  1. extractionextract with ether
  2. customisolate the crude product
  3. customChromatograph on Grade I neutral alumina (50 g) and recrystallize from ether-hexane

Sources & evidence

ORD record
ord-7cc26a2e2a184b5ca8a1b63609f85906
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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