Hydrochloric Acid → 5-Acetylfuro(2,3-c)pyridine

HRID 1251564Notes

Reaction equation

HRID 1251564 reaction equation
[O:1]=[C:2]([C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][O:14][C:11]2=[CH:12][N:13]=1)[CH2:3]C(OC)=O.O=C(C1C=C2C=COC2=CN=1)CC(OCC)=O.O=C(C1C=C2C=COC2=CN=1)CC(OC(C)(C)C)=O.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:2]([C:8]1[CH:9]=[C:10]2[CH:16]=[CH:15][O:14][C:11]2=[CH:12][N:13]=1)(=[O:1])[CH3:3]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9859266Methyl beta-oxo-5-furo[2,3-c]pyridinepropionateHCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionateHCID 18324178Tert-butyl beta-oxo-5-furo[2,3-c]pyridinepropionate

Product 1

HCID 97939025-Acetylfuro(2,3-c)pyridineYield 78%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The 971 mg of the mixture of methyl β-oxo-5-furo[2,3-c]pyridinepropionate, ethyl β-oxo-5-furo[2,3-c]pyridinepropionate, and tert-butyl β-oxo-5-furo[2,3-c]pyridinepropionate (molar ratio of 55:44:1) obtained in Example 9 was dissolved in 20 mL of toluene, and 1.04 g of 35% hydrochloric acid was added at room temperature with stirring. After addition, the reaction mixture was heated to 60° C., and a reaction was carried out for 3 hours with stirring. The reaction solution was then cooled to room temperature and was neutralized with 8.40 g of 5% sodium hydroxide aqueous solution. 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 629 mg of 5-acetylfuro[2,3-c]pyridine in a purity of 99% by HPLC (78% yield from 5-ethoxycarbonylfuro[2,3-c]pyridine).

Workup

  1. additionAfter addition
  2. stirringwith stirring
  3. temperatureThe reaction solution 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-d768c3b1eb2a45df8eca97b1edc3596e
Source dataset
uspto-grants-2002_01
Patent number
US06342606B2

Reaction notes

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