Ethanol → Ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate

HRID 423033Notes

Reaction equation

HRID 423033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.Cl.[O:16]([NH2:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].[CH2:25](O)[CH3:26]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:18][O:16][CH3:17])[CH2:9][CH2:10][C:11]([O:13][CH2:25][CH3:26])=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 776043-(4-Chlorobenzoyl)propionic acidHCID 521874O-Methylhydroxylamine hydrochloride

Product 1

HCID 86632052Ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoateYield 70.6%

Conditions

Temperature
80 °C

Procedure

4-(4-Chlorophenyl)-4-oxobutanoic acid (2.0 g, 9.41 mmol), methoxylamine hydrochloride (0.982 g, 11.76 mmol) and sodium carbonate (0.472 ml, 11.29 mmol) in ethanol (30 ml) were stirred and heated at 80° C. for 4 hours. The resulting mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated by evaporation then purified by flash silica chromatography, eluting with 15% TBME in isohexane. Pure fractions were evaporated to dryness to afford ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (1.790 g, 70.6%) as a colourless oil.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated by evaporation
  4. customthen purified by flash silica chromatography
  5. washeluting with 15% TBME in isohexane
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-35ab9e300c3e4a83afc048ea52fcb5a0
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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