Ammonium Chloride → Ethanone, 1-furo[2,3-c]pyridin-5-yl- (9CI)

HRID 1251560Notes

Reaction equation

HRID 1251560 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 9793902Ethanone, 1-furo[2,3-c]pyridin-5-yl- (9CI)Yield 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-b236aa7b46584658b9e0b1af10856484
Source dataset
uspto-grants-2002_01
Patent number
US06342606B2

Reaction notes

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