Diethyl Oxalate → Ethyl 4-(4-chlorophenyl)-2,4-dioxobutanoate

HRID 476088Notes

Reaction equation

HRID 476088 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12](OCC)(=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH2:10][C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 7467P-ChloroacetophenoneHCID 5360545Sodium

Product 1

HCID 602482Ethyl 4-(4-chlorophenyl)-2,4-dioxobutanoateYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (0.143 g, 6.21 mmol) was dissolved into ethanol (3 mL) and the resulting solution was cooled with an ice bath. A mixture of 1-(4-chlorophenyl)ethanone (0.756 mL, 5.65 mmol) and diethyl ethanedioate (0.766 mL, 5.65 mmol) were added dropwise, and the reaction mixture was stirred for 16 h. The reaction mixture was quenched with ice water (5 mL) and acidified to ˜pH 3 with 1N HCl. The precipitate was collected by filtration and dried under high vacuum to give 1.39 g (97%) of product. LCMS E-S (M+H)=255.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (m, 3H), 4.27 (d, J=6.57 Hz, 2H), 7.60 (d, J=7.58 Hz, 2H), 8.02 (d, J=6.57 Hz, 2H).

Workup

  1. temperaturethe resulting solution was cooled with an ice bath
  2. additionwere added dropwise
  3. customThe reaction mixture was quenched with ice water (5 mL)
  4. filtrationThe precipitate was collected by filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-80770c1c6e3e49cebdd6a2bf42d19de2
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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