Hydrochloric Acid → Ethyl 4-(furan-2-yl)-2,4-dioxobutanoate

HRID 968361Notes

Reaction equation

HRID 968361 reaction equation
[H-].[Na+].[C:3]([O:10][CH2:11][CH3:12])(=[O:9])[C:4]([O:6]CC)=O.[C:13]([C:16]1[O:17][CH:18]=[CH:19][CH:20]=1)(=[O:15])[CH3:14].Cl>O1CCCC1>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:13](=[O:15])[CH2:14][C:4](=[O:6])[C:3]([O:10][CH2:11][CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 145052-AcetylfuranHCID 24758Sodium hydride

Product 1

HCID 3006753Ethyl 4-(furan-2-yl)-2,4-dioxobutanoateYield 58.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of sodium hydride (5.4 g of 60% dispersion in mineral oil, 136 mmol, mineral oil was removed by washing twice with hexanes) in 100 mL of tetrahydrofuran at ambient temperature was added diethyl oxalate (12.3 mL, 91 mmol). To this mixture was added 2-acetylfuran (5.0 g, 45 mmol) as a solution in 25 mL of tetrahydrofuran. The resulting mixture was stirred at 70° C. for 1 h. The reaction was cooled to room temperature and then 10% HCl was added slowly until the solution was acidic. The tetrahydrofuran was removed in vacuo and the residue was taken up in ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated to afford 5.5 g (58%) of the title compound which was used without purification.

Workup

  1. customwas removed
  2. washby washing twice with hexanes) in 100 mL of tetrahydrofuran at ambient temperature
  3. temperatureThe reaction was cooled to room temperature
  4. customThe tetrahydrofuran was removed in vacuo
  5. washThe organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-545425f9f2be484cb6e5010117eefcc5
Source dataset
uspto-grants-2005_10
Patent number
US06958356B2

Reaction notes

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