Hydrochloric Acid → Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoate

HRID 1990768Notes

Reaction equation

HRID 1990768 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].Cl>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH2:12][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 74764'-MethoxyacetophenoneHCID 24758Sodium hydride

Product 1

HCID 287267Ethyl 4-(4-methoxyphenyl)-2,4-dioxobutanoateYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

With cooling with ice, 4.00 g (0.10 mol) of 65% oily sodium hydride was added to a DMF solution (200 ml) of 7.51 g (0.05 mol) of 4′-methoxyacetophenone and 8.77 g (0.06 mol) of diethyl oxalate, and stirred overnight at 100° C. in a nitrogen atmosphere. Aqueous 2 N hydrochloric acid solution was added to the reaction liquid, extracted with ethyl acetate, and the organic layer was washed with saturated saline water, dried and then concentrated under reduced pressure. Thus concentrated under reduced pressure, the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1) to obtain 12.52 g (yield: 100%) of ethyl 4-(4-methoxyphenyl)-2,4-dioxobutyrate as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic layer was washed with saturated saline water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. concentrationThus concentrated under reduced pressure
  6. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4a0d6cc1b0814e01949f541b12e4d235
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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