Diethyl Oxalate → Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

HRID 1896688Notes

Reaction equation

HRID 1896688 reaction equation
[O-]CC.[Na+].[C:5]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)(=[O:7])[CH3:6].[C:13](OCC)(=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[CH2:17]([O:16][C:14](=[O:15])[C:13](=[O:19])[CH2:6][C:5]([C:8]1[O:9][CH:10]=[CH:11][CH:12]=1)=[O:7])[CH3:18]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 145052-AcetylfuranHCID 2723922Sodium ethoxide

Product 1

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium ethoxide (6.81 g) in absolute ethanol (200 mL). was slowly added 2-acetylfuran (5.01 mL) at 0° C. The resulting solution was stirred at 0° C. for 2 hours, and diethyl oxalate (9.30 mL) was slowly added to the solution. The resulting solution was stirred for 18 hours, and the reaction was quenched with 1N hydrochloric acid solution. The resulting mixture was concentrated under reduced pressure, and residue was then extracted with methylene chloride. An organic phase was dried over anhydrous sodium sulfate, filtered, and then concentrated under reduced pressure to give 10.0 g of 4-furan-2-yl-2,4-dioxo-butyric acid ethyl ester. This concentrate was used in the next steps without further purification.

Workup

  1. customat 0° C
  2. stirringThe resulting solution was stirred for 18 hours
  3. customthe reaction was quenched with 1N hydrochloric acid solution
  4. concentrationThe resulting mixture was concentrated under reduced pressure, and residue
  5. extractionwas then extracted with methylene chloride
  6. dry with materialAn organic phase was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96328210102d44c094770e0255a3e8de
Source dataset
uspto-grants-2013_08
Patent number
US08518978B2

Reaction notes

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