Hydrochloric Acid → 13beta-Propyl-17beta-hydroxy-gon-4-en-3-one

HRID 1077184Notes

Reaction equation

HRID 1077184 reaction equation
Cl.[CH2:2]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C:14]4[CH2:15][CH:16]=[C:17]([O:22]C)[CH2:18][C:19]=4[CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])[CH2:3][CH3:4].CO>O>[CH2:2]([C@:5]12[CH2:13][CH2:12][C@@H:11]3[C@@H:14]4[C:19]([CH2:20][CH2:21][C@H:10]3[C@@H:9]1[CH2:8][CH2:7][C@@H:6]2[OH:24])=[CH:18][C:17](=[O:22])[CH2:16][CH2:15]4)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6814424813beta-n-Propyl-3-methoxy-gona-2,5(10)-dien-17beta-ol

Product 1

HCID 6814332113beta-Propyl-17beta-hydroxy-gon-4-en-3-oneYield 13.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 3N hydrochloric acid (1 cc.) to a solution of 13β-n-propyl-3-methoxy-gona-2,5(10)-dien-17β-ol (0.61 g.) in boiling methanol (70 cc.) and cool the mixture immediately and allow to stand for 41/2 hours. Pour the product into water (300 cc.) and extract the mixture with ether; work up in the usual way to give as residue an amorphous solid (0.6 g.). Crystallize this solid from a mixture of ether and hexane. Take up the resulting solid in benzene (20 cc.) and chromatograph on a column of neutral alumina. Elute the product with ether and recrystallize from a mixture of ether and hexane to obtain 13β-n-propyl-17β-hydroxy-gon-4-en-3-one (0.08 g.), mp. 126°-7°; ultraviolet absorption peak at 240 mμ (ε15,000); infrared absorption peaks at 2.92, 6.01, 6.20 μ. Evaporation of the mother liquors gives a second, polymorphic, form of the same substance (0.17 g.), m.p. 144°-5° , having ultraviolet and infrared spectra identical with the first material; a mixture of the two forms has m.p. 144°-5°.

Workup

  1. temperaturecool the mixture immediately
  2. custom2 hours
  3. extractionextract the mixture with ether
  4. customwork up in the usual way to give as residue an amorphous solid (0.6 g.)
  5. customCrystallize this solid
  6. additionfrom a mixture of ether and hexane
  7. washElute the product with ether
  8. customrecrystallize from a mixture of ether and hexane

Sources & evidence

ORD record
ord-ba8e9e360d0a4bc8b505d223ae501de5
Source dataset
uspto-grants-1976_05
Patent number
US03959322

Reaction notes

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