Triethylamine → 2-[1-(Allyloxyimino)butyl]-5,5-dimethyl-3-hydroxy-4-phenyl cyclohex-2-ene-1-one

HRID 1031323Notes

Reaction equation

HRID 1031323 reaction equation
C(N(CC)CC)C.[C:8]([C:13]1[C:14](=[O:28])[CH2:15][C:16]([CH3:27])([CH3:26])[CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]=1[OH:19])(=O)[CH2:9][CH2:10][CH3:11].Cl.[CH2:30]([O:33][NH2:34])[CH:31]=[CH2:32]>C(O)C>[CH2:30]([O:33][N:34]=[C:8]([C:13]1[C:14](=[O:28])[CH2:15][C:16]([CH3:27])([CH3:26])[CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:18]=1[OH:19])[CH2:9][CH2:10][CH3:11])[CH:31]=[CH2:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 221675352-Butyryl-5,5-dimethyl-3-hydroxy-4-phenylcyclohex-2-ene-1-one

Product 1

HCID 1361385052-[1-(Allyloxyimino)butyl]-5,5-dimethyl-3-hydroxy-4-phenyl cyclohex-2-ene-1-oneYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (1.2 g) was added to a solution of 2-butyryl-5,5-dimethyl -3-hydroxy-4-phenyl cyclohex-2-ene-1-one (2.8 g) and O-allylhydroxylamine hydrochloride (1.2 g) in ethanol (50 ml). After stirring at ambient temperature overnight, the ethanol was evaporated in vacuo, water was added to the residue and the aqueous solution extracted with methylene chloride. After drying the organic extracts over anhydrous magnesium sulphate, the methylene chloride was evaporated in vacuo. The residue was chromatographed on a silica gel column using 5% (v/v) diethyl ether-methylene chloride as eluant to give the title compound (2.1 g) as a viscous, colourless oil.

Workup

  1. customthe ethanol was evaporated in vacuo, water
  2. additionwas added to the residue
  3. extractionthe aqueous solution extracted with methylene chloride
  4. dry with materialAfter drying the organic extracts over anhydrous magnesium sulphate
  5. customthe methylene chloride was evaporated in vacuo
  6. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-869c72ad4ddc4d27a5b19b158b7d829b
Source dataset
uspto-grants-1990_09
Patent number
US04954160

Reaction notes

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