Ethanol → HCID 136005283, compound

HRID 1382169Notes

Reaction equation

HRID 1382169 reaction equation
Cl.[CH2:2]([O:5][NH2:6])[CH:3]=[CH2:4].[OH-].[Na+].[OH:9][C:10]1[CH2:15][CH:14]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([Br:24])[C:17]=2[CH3:25])[CH2:13][C:12](=[O:26])[C:11]=1[C:27](=O)[CH2:28][CH3:29].C(O)C>O>[CH2:2]([O:5][N:6]=[C:27]([C:11]1[C:12](=[O:26])[CH2:13][CH:14]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[C:18]([Br:24])[C:17]=2[CH3:25])[CH2:15][C:10]=1[OH:9])[CH2:28][CH3:29])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 178458834HCID 178458834, compound

Product 1

HCID 136005283HCID 136005283, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Allyloxyamine hydrochloride (0.17 g) and then a solution of sodium hydroxide (0.06 g) in water (1 ml) were added to a stirred mixture of 3-hydroxy-2-propionyl-5-(3-bromo-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.50 g, 1.37 mmole) and 95% ethanol. The progress of the reaction was monitored using thin layer chromatography on silica gel (eluant dichloromethane). On completion of the reaction the ethanol was removed by evaporation under reduced pressure and the residue was extracted with dichloromethane. The organic extract was washed with aqueous 5% hydrochloric acid and then with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure to give the product, 2-[1-(allyloxyimino)propyl]-3-hydroxy-5-(3-bromo-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.33 g, 57.4%) as an oil.

Workup

  1. customwas removed by evaporation under reduced pressure
  2. extractionthe residue was extracted with dichloromethane
  3. extractionThe organic extract
  4. washwas washed with aqueous 5% hydrochloric acid
  5. dry with materialwith water and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4cbfdb4bc94642dc9d1478b67787c40d
Source dataset
uspto-grants-1989_02
Patent number
US04806141

Reaction notes

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