Citric Acid → t-Butyl2-acetyl-4-(4-ethylphenyl)-3-oxobutyrate

HRID 1625854Notes

Reaction equation

[Cl-].[Mg+2].[Cl-].[C:4]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:5][C:6]([CH3:8])=[O:7].[CH2:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24](Cl)=[O:25])=[CH:19][CH:18]=1)[CH3:16].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.N1C=CC=CC=1>[C:6]([CH:5]([C:24](=[O:25])[CH2:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:15][CH3:16])=[CH:18][CH:19]=1)[C:4]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:7])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of magnesium chloride (1.74 g) in dichloromethane (30 ml) was cooled to 0° C., and thereto were added t-butyl acetoacetate (3.03 ml) and pyridine (2.96 ml), and successively was added a solution of the above 4-ethylphenylacetyl chloride in dichloromethane (30 ml). The mixture was stirred at the same temperature for 2.5 hours, and an aqueous citric acid solution was added thereto. The mixture was extracted with chloroform. The extract was washed with brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give t-butyl 2-acetyl-4-(4-ethylphenyl)-3-oxobutyrate (4.75 g) as pale yellow oil. APCI-Mass m/Z 322 (M+NH4).

Workup

extractionThe mixture was extracted with chloroform
washThe extract was washed with brine
dry with materialdried over sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

Sources & evidence

ORD record: ord-4915531292404465b1541f97a6d917a9
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785403B2

Reaction notes

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