Sodium Hydroxide → 5-Acetylfuro(2,3-c)pyridine

HRID 1251566Notes

Reaction equation

HRID 1251566 reaction equation
[O:1]=[C:2]([C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][O:15][C:12]2=[CH:13][N:14]=1)[CH2:3]C(OCC)=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:2]([C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][O:15][C:12]2=[CH:13][N:14]=1)(=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionate

Product 1

HCID 97939025-Acetylfuro(2,3-c)pyridineYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl β-oxo-5-furo[2,3-c]pyridinepropionate (583 mg, 2.5 mmol) obtained in Example 7 was dissolved in 10 mL of toluene, and 3 g of 10% sodium hydroxide aqueous solution was added with stirring. After addition, the reaction mixture was heated to 60° C., and a reaction was carried out for 8 hours with stirring. It was then cooled 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, giving 205 mg (51% yield) of 5-acetylfuro[2,3-c]pyridine in a purity of 99% by HPLC.

Workup

  1. additionAfter addition
  2. stirringwith stirring
  3. temperatureIt was then cooled to room temperature
  4. customthe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with 5 mL of methylene chloride
  6. dry with materialthe combined organic layer was dried with anhydrous magnesium sulfate
  7. concentrationconcentrated in a rotary evaporator
  8. customThe resulting solids were recrystallized from a mixed solvent of toluene-hexane

Sources & evidence

ORD record
ord-7f7079e456be43dbac8eb443e080ed4e
Source dataset
uspto-grants-2002_01
Patent number
US06342606B2

Reaction notes

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