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

HRID 1415002Notes

Reaction equation

HRID 1415002 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 4 1/2 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 (ε 15,000); 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. customto stand for 4 1/2 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-325a63e8f7a54a51bb2c1fdc9a9d6648
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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