Ethanol → HCID 73680026, compound

HRID 435063Notes

Reaction equation

HRID 435063 reaction equation
[CH3:1][C:2]1([CH3:19])[C:6](=O)[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1.C(O)C.C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:30][OH:31]>O.CC(C)=O>[CH3:1][C:2]1([CH3:19])[C:6](=[N:30][OH:31])[CH2:5][C:4]([CH2:10][O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH2:8][CH3:9])[O:3]1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium Carbonate2×HCID 443297Hydroxyamine hydrochlorideHCID 20490674HCID 20490674, compound

Product 1

HCID 73680026HCID 73680026, compoundYield 94.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The ketone of Example 6 (1 g), ethanol (20 ml) hydroxylamine hydrochloride (280 mg) and potassium carbonate (330 mg) were refluxed together for 2 hours. Thin layer chromatography, using 15% acetone in petrol as eluant, showed partial conversion. Additional quantities of hydroxylamine hydrochloride (280 mg) and potassium carbonate (330 mg) were added three times, with refluxing for 2 hours after each addition. Water was then added, and the mixture was extracted with diethyl ether. The ether extract was dried over magnesium sulphate and evaporated and the residue was purified on a silica gel column using 5% acetone in petrol as eluant to give 1 g (94%) of the desired product.

Workup

  1. temperaturewith refluxing for 2 hours
  2. additionafter each addition
  3. extractionthe mixture was extracted with diethyl ether
  4. extractionThe ether extract
  5. dry with materialwas dried over magnesium sulphate
  6. customevaporated
  7. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-8f5411704fad4ada895b96b42f0c9dcc
Source dataset
uspto-grants-1983_08
Patent number
US04400198

Reaction notes

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