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

HRID 1415044Notes

Reaction equation

HRID 1415044 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; λmax. 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-366cf5ac5bf54fd482ca521e94ec47df
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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