Diethyl Ether → (E)-ethyl 3-(furan-3-yl)acrylate

HRID 611067Notes

Reaction equation

HRID 611067 reaction equation
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[O:17]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18]1.CCOCC>C1C=CC=CC=1>[O:17]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:18]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 103513-FuraldehydeHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydride

Product 1

HCID 10103508(E)-ethyl 3-(furan-3-yl)acrylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 17.7 g (78.8 mmol) of ethyl diethylphosphonoacetate in 150 ml of benzene, 2.89 g (72.2 mmol) of sodium hydride (60% in oil) was added under ice-cooling, followed by stirring for 30 minutes. To this solution, a solution of 6.308 g (65.65 mmol) of 3-furaldehyde in 50 ml of benzene was added dropwise, followed by stirring at room temperature for 30 minutes and refluxing for 30 minutes. After the reaction mixture was cooled to room temperature, ether was added; the mixture was then washed with water. The ether solution was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=9/1) to yield the desired product.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 30 minutes
  3. temperaturerefluxing for 30 minutes
  4. washthe mixture was then washed with water
  5. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resulting crude product was purified by silica gel column chromatography (hexane to hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-afe5c1d3b79a4e8193a80a8094624352
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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