Furfural → HCID 66755973, compound

HRID 1643778Notes

Reaction equation

HRID 1643778 reaction equation
[CH3:1]C[O-].[Na+].[O:5]1[CH:9]=[CH:8][CH:7]=[C:6]1C=O.[C:12]([O:21]CC)(=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[CH2:18]([O:17][C:15]([C:14](=[CH:1][C:8]1[CH:7]=[CH:6][O:5][CH:9]=1)[CH2:13][C:12]([OH:21])=[O:20])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 7362FurfuralHCID 31249Diethyl SuccinateHCID 2723922Sodium ethoxide

Product 1

HCID 66755973HCID 66755973, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (6.5 g, 95 mmol) was added under vigorous stirring to a solution of 2-furaldehyde (10 g, 79 mmol) and diethyl succinate (27.6 g, 158 mmol) in ethanol (300 mL). The reaction mixture was refluxed for 3 h and evaporated in vacuum (˜20 mmHg) at 50° C. until the solvent distillation ceased. The obtained residue was diluted with 200 mL of 10% HCl and 300 mL of ethyl acetate. The mixture was shaken. The organic layer was separated, diluted with 200 mL of a saturated aqueous solution of NaHCO3, and shaken. The aqueous layer was separated, neutralized by 10% HCl to pH 2, and subjected to extraction by 400 mL of ethyl acetate. The organic layer was evaporated in vacuum (˜20 mmHg) at 60° C. and chromatographed on a layer of silica gel (200×150 mm) with hexane/ethyl acetate mixture (1:1). Fractions containing the target product were collected and evaporated in vacuum to give the product 9.3 g (38 mmol, 49%) as a light-brown oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customevaporated in vacuum (˜20 mmHg) at 50° C. until the solvent distillation
  3. additionThe obtained residue was diluted with 200 mL of 10% HCl and 300 mL of ethyl acetate
  4. customThe organic layer was separated
  5. additiondiluted with 200 mL of a saturated aqueous solution of NaHCO3
  6. stirringshaken
  7. customThe aqueous layer was separated
  8. extractionsubjected to extraction by 400 mL of ethyl acetate
  9. customThe organic layer was evaporated in vacuum (˜20 mmHg) at 60° C.
  10. customchromatographed on a layer of silica gel (200×150 mm) with hexane/ethyl acetate mixture (1:1)
  11. additionFractions containing the target product
  12. customwere collected
  13. customevaporated in vacuum

Sources & evidence

ORD record
ord-24494b4dbd7c41f98082d3a75f6bb75f
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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