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

HRID 423071Notes

Reaction equation

HRID 423071 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 97%

Procedure

4-(4-Chlorophenyl)-4-oxobutanoic acid (10 g, 47.03 mmol), methoxylamine hydrochloride (4.91 g, 58.79 mmol) and sodium carbonate (5.98 g, 56.44 mmol) in ethanol (150 mL) were stirred for 4 hrs at 80° C. The mixture was then cooled to room temperature before being filtered. The filtrate was concentrated by evaporation and purified by flash silica chromatography (eluent 20-50% EtOAc/iso-hexane). Pure fractions were evaporated to dryness to afford ethyl 4-(4-chlorophenyl)-4-(methoxyimino)butanoate (12.33 g, 97%) as an orange transparent liquid.

Workup

  1. filtrationbefore being filtered
  2. concentrationThe filtrate was concentrated by evaporation
  3. custompurified by flash silica chromatography (eluent 20-50% EtOAc/iso-hexane)
  4. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-1eeb4ce626954ab78f34d1f67bd4364a
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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