HCID 14883204, compound → HCID 69869398, compound

HRID 1415024Notes

Reaction equation

HRID 1415024 reaction equation
[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C@@H:4]2[OH:20])=[CH:16][CH2:15][CH2:14][CH2:13]4)[CH3:2]>CC(C)=O.[Cr](O)(O)(=O)=O>[CH2:1]([C@:3]12[CH2:11][CH2:10][C@@H:9]3[C@@H:12]4[C:17]([CH2:18][CH2:19][C@H:8]3[C@@H:7]1[CH2:6][CH2:5][C:4]2=[O:20])=[CH:16][CH2:15][CH2:14][CH2:13]4)[CH3:2]

Participants

4

Reactant 1

HCID 14883204HCID 14883204, compound

Product 1

HCID 69869398HCID 69869398, compoundYield 83.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 24425Chromic AcidSolvent

Procedure

Dissolve 13β-ethyl-gon-4-en-17β-ol (0.29 g.) in acetone (40 cc.) and 8N-chromic acid dropwise with stirring until the solution becomes permanently orange and then add isopropanol (3 cc.) and evaporate the solution to small bulk (ca. 5 cc.). Add water and extract the mixture with ether. Wash, dry and evaporate the ethereal solution to obtain 13β-ethyl-gon-4-en-17-one (0.24 g.), m.p. 101°-102° C. Purify by recrystallization from methanol to obtain the pure product, m.p. 102.5°-103.5° C.

Workup

  1. customadd isopropanol (3 cc.) and evaporate the solution to small bulk (ca. 5 cc.)
  2. extractionAdd water and extract the mixture with ether
  3. washWash
  4. customdry
  5. customevaporate the ethereal solution

Sources & evidence

ORD record
ord-4c435bd4a49046099cb34ab494163fd3
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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