Acetic Acid → Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionate

HRID 1386656Notes

Reaction equation

HRID 1386656 reaction equation
C(O[C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[CH:10][N:11]=1)=[O:5])C.[O-]CC.[Na+].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20].C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:5]=[C:4]([C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][O:12][C:9]2=[CH:10][N:11]=1)[CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl Acetate2×HCID 2723922Sodium ethoxideHCID 11074225HCID 11074225, compound

Product 1

HCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

5-Ethoxycarbonylfuro[2,3-c]pyridine(956 mg, 5.0 mmol) was dissolved in 10 mL of toluene, 510 mg (7.5 mmol) of sodium ethoxide was added at room temperature to the solution, and 661 mg (7.5 mmol) of ethyl acetate was then added dropwise at room temperature with stirring. After all the ethyl acetate had been added, the reaction mixture was heated to 80° C., and a reaction was carried out for 4 hours. The reaction solution was then cooled to 5° C. and was neutralized with 450 mg (7.5 mmol) of acetic acid as the temperature was held 5-10° C., the solution was stirred for 30 minutes as the temperature was maintained, 1 mL water was then added, and the solution was returned to room temperature. The organic layer was separated, the aqueous layer was extracted twice with 5 mL of methylene chloride, and the combined organic layer was dried with anhydrous magnesium sulfate and then concentrated in a rotary evaporator, and the resulting solids were recrystallized from a mixed solvent of toluene-hexane, giving 840 mg (72% yield) of ethyl β-oxo-5-furo[2,3-c]pyridinepropionate in a purity of 99% by HPLC.

Workup

  1. additionwas then added dropwise at room temperature
  2. temperatureThe reaction solution was then cooled to 5° C.
  3. customwas held 5-10° C.
  4. stirringthe solution was stirred for 30 minutes as the temperature
  5. temperaturewas maintained
  6. customwas returned to room temperature
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted twice with 5 mL of methylene chloride
  9. dry with materialthe combined organic layer was dried with anhydrous magnesium sulfate
  10. concentrationconcentrated in a rotary evaporator
  11. customthe resulting solids were recrystallized from a mixed solvent of toluene-hexane

Sources & evidence

ORD record
ord-6eaca9d918d04bc2a651add5d378ab99
Source dataset
uspto-grants-2001_07
Patent number
US06265580B1

Reaction notes

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