Ethanol → Ethyl alpha-oxofuran-2-acetate

HRID 253984

Reaction equation

HRID 253984 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([OH:9])=[O:8].[CH3:11][CH2:12]O.OS(O)(=O)=O>C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[C:7]([O:9][CH2:11][CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 738462-Furylglyoxylic acid

Product 1

HCID 74230Ethyl alpha-oxofuran-2-acetateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
65 °C

Procedure

2-(Furan-2-yl)-2-oxoacetic acid (15.0 g, 107 mmol) was dissolved in chloroform (420 mL) and treated with EtOH (165 mmol) and H2SO4 (1 mL). The reaction was heated to 65° C. overnight, at which point LC-MS indicated disappearance of starting material and product formation. The crude reaction was cooled and washed with sat. aq. NaHCO3 (3×100 mL) and brine (100 mL). The organics were concentrated to provide ethyl 2-(furan-2-yl)-2-oxoacetate (15.5 g, 64%) as a brown oil, which was used without further purification.

Workup

  1. customThe crude reaction
  2. temperaturewas cooled
  3. washwashed with sat. aq. NaHCO3 (3×100 mL) and brine (100 mL)
  4. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-eff0ec7040a4433999c4862567c12765
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Linked notes

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