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

HRID 1386654
Notes
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Reaction equation

HRID 1386654 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 11074225Ethyl furo[2,3-c]pyridine-5-carboxylateHCID 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-e7d4704e4c22441884954fc251882821
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06265580B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes