Ammonium Chloride → 5-Acetylfuro(2,3-c)pyridine

HRID 1873074Notes

Reaction equation

HRID 1873074 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.C[Li].[CH2:17](OCC)C.[Cl-].[NH4+]>O1CCCC1>[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])[CH3:17]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11074225HCID 11074225, compoundHCID 178467906HCID 178467906, compound

Product 1

HCID 97939025-Acetylfuro(2,3-c)pyridineYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

5-Ethoxycarbonylfuro[2,3-c]pyridine obtained in Example 2(3.82 g, 20.0 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -30° C. To the cooled solution, 22.0 mL (22.0 mol) of 1.0 M solution of methyllithium/diethyl ether was added, and the solution was stirred for 2 hours at the same temperature, the reaction mixture was then poured into 100 mL of 5% ammonium chloride aqueous solution which had been cooled on ice, and the product was extracted twice with 100 mL of ethyl acetate. After washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water, the extract was concentrated to give 3.12 g of crude product. This product was purified by column chromatography on silica gel, giving 2.48 g (77.0% yield) of 5-acetylfuro[2,3-c]pyridine.

Workup

  1. temperaturehad been cooled on ice
  2. extractionthe product was extracted twice with 100 mL of ethyl acetate
  3. washAfter washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water
  4. concentrationthe extract was concentrated
  5. customto give 3.12 g of crude product
  6. customThis product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5dd61b5a322145c4a3de466276f956e9
Source dataset
uspto-grants-2000_08
Patent number
US06111111

Reaction notes

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