Chromic Acid → HCID 53667012, compound

HRID 1415025Notes

Reaction equation

HRID 1415025 reaction equation
[Cr](O)(O)(=O)=O.[CH2:6]([C@:9]12[CH2:17][CH2:16][C@@H:15]3[C@@H:18]4[C:23]([CH2:24][CH2:25][C@H:14]3[C@@H:13]1[CH2:12][CH2:11][C@@H:10]2[OH:26])=[CH:22][CH2:21][CH2:20][CH2:19]4)[CH2:7][CH3:8]>CC(C)=O>[CH2:6]([C@:9]12[CH2:17][CH2:16][C@@H:15]3[C@@H:18]4[C:23]([CH2:24][CH2:25][C@H:14]3[C@@H:13]1[CH2:12][CH2:11][C:10]2=[O:26])=[CH:22][CH2:21][CH2:20][CH2:19]4)[CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24425Chromic AcidHCID 68143216HCID 68143216, compound

Product 1

HCID 53667012HCID 53667012, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 8N chromic acid dropwise with stirring to a solution of 13β-n-propyl-gon-4-en-17β-ol in acetone (100 cc.) until the solution becomes permanently orange. Add isopropanol (10 cc.) and potassium carbonate (5 g.), filter and evaporate the filtrate to dryness. Filter the residue in benzene-ether (1:1) through neutral alumina (20 g.), evaporate and recrystallize the product from methanol to obtain 13β-n-propyl-gon-4-en-17-one. Recrystallize from ether-hexane to obtain the pure product, m.p. 89°-90° C.

Workup

  1. filtrationAdd isopropanol (10 cc.) and potassium carbonate (5 g.), filter
  2. customevaporate the filtrate to dryness
  3. filtrationFilter the residue in benzene-ether (1:1) through neutral alumina (20 g.)
  4. customevaporate
  5. customrecrystallize the product from methanol

Sources & evidence

ORD record
ord-8e6b6366ae834b2a8b973d2ddcdde342
Source dataset
uspto-grants-1977_01
Patent number
US04002746

Reaction notes

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