Phenylacetyl chloride → 2-Acetyl-3-oxo-4-phenyl-butyric acid methyl ester

HRID 2279640Notes

Reaction equation

HRID 2279640 reaction equation
[OH-].[Na+].[CH3:3][C:4]([CH2:6][C:7]([O:9][CH3:10])=[O:8])=[O:5].[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH3:10][O:9][C:7](=[O:8])[CH:6]([C:4](=[O:5])[CH3:3])[C:18](=[O:19])[CH2:17][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 7757Methyl acetoacetateHCID 14798Sodium Hydroxide

Product 1

HCID 595798522-Acetyl-3-oxo-4-phenyl-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

NaOH (10 N, 4.4 mL, 44 mmol) in H2O is added to a solution of MeCOCH2COOMe (5 g, 43.1 mmol) in THE at RT. PhCH2COCl is added dropwise to the mixture and the mixture is stirred for 14 h. The mixture is extracted with EtOAc (2×30 mL). The organic phase is dried. The product is purified by silica gel column chromatography using 3-5% EtOAc in hexane to afford the title compound.

Workup

  1. extractionThe mixture is extracted with EtOAc (2×30 mL)
  2. customThe organic phase is dried
  3. customThe product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6fe6ffc40f134228a75776eaf7723a58
Source dataset
uspto-grants-2015_09
Patent number
US09133204B2

Reaction notes

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