HCID 68144537, compound → HCID 68143867, compound

HRID 1415004Notes

Reaction equation

HRID 1415004 reaction equation
[CH:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C:13]4[CH2:14][CH:15]=[C:16]([O:21]C)[CH2:17][C:18]=4[CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])([CH3:3])[CH3:2]>CO.Cl.O>[CH:1]([C@:4]12[CH2:12][CH2:11][C@@H:10]3[C@@H:13]4[C:18]([CH2:19][CH2:20][C@H:9]3[C@@H:8]1[CH2:7][CH2:6][C@@H:5]2[OH:23])=[CH:17][C:16](=[O:21])[CH2:15][CH2:14]4)([CH3:3])[CH3:2]

Participants

5

Reactant 1

HCID 68144537HCID 68144537, compound

Product 1

HCID 68143867HCID 68143867, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 13β-isopropyl-3-methoxy-gona-2,5(10)-dien-17β-ol in methanol (36 cc.), concentrated hydrochloric acid (2.4 cc.) and water (1.6 cc.) and allow the mixture to stand at room temperature for 2 hours. Add water and collect the product in ether. Wash, dry and evaporate the ethereal solution and chromatograph the residue on alumina (30 g.). Elute with benzene containing 30% ether and evaporate the solvent to obtain 13β-isopropyl-17β-hydroxy-gon-4-en-3-one as a gum; infrared absorption peak at 5.99 μ; ultraviolet absorption peak at 249 mμ (ε12,000).

Workup

  1. customAdd water and collect the product in ether
  2. washWash
  3. customdry
  4. customevaporate the ethereal solution and chromatograph the residue on alumina (30 g.)
  5. washElute with benzene containing 30% ether
  6. customevaporate the solvent

Sources & evidence

ORD record
ord-60c9d6e11ed64863ad92153f0b60f154
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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