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

HRID 1251563Notes

Reaction equation

HRID 1251563 reaction equation
[O-]CC.[Na+].[C:5]([O:8][C:9](C)(C)[CH3:10])(=[O:7])[CH3:6].C(O[C:16]([C:18]1[CH:19]=[C:20]2[CH:26]=[CH:25][O:24][C:21]2=[CH:22][N:23]=1)=[O:17])C.C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:17]=[C:16]([C:18]1[CH:19]=[C:20]2[CH:26]=[CH:25][O:24][C:21]2=[CH:22][N:23]=1)[CH2:6][C:5]([O:8][CH2:9][CH3:10])=[O:7]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10908tert-Butyl acetateHCID 2723922Sodium ethoxideHCID 11074225HCID 11074225, compound

Product 1

HCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionateYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

As 510 mg (7.5 mmol) of sodium ethoxide was stirred in 5 mL toluene, 1.16 g (10.0 mmol) of t-butyl acetate was added dropwise at room temperature to the solution. Then, 956 mg (5.0 mmol) of 5-ethoxycarbonylfuro[2,3-c]pyridine dissolved in 5 mL of toluene was added dropwise at room temperature to the above solution. After all the solution had been added, the reaction mixture was heated to 60° C., and a reaction was carried out for 3 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. The resulting solids were recrystallized from a mixed solvent of toluene-hexane mixture, giving 933 mg (80% yield) of ethyl β-oxo-5-furo[2,3-c]pyridinepropionate in a purity of 99% by HPLC.

Workup

  1. additionwas added dropwise at room temperature to the above solution
  2. additionAfter all the solution had been added
  3. temperatureThe reaction solution was then cooled to 5° C.
  4. customwas held 5-10° C.
  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 mixture

Sources & evidence

ORD record
ord-04c49a74fd4946c29d510bfd49140aff
Source dataset
uspto-grants-2002_01
Patent number
US06342606B2

Reaction notes

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