Ethyl 2-pyridinecarboxylate → 2-phenyl-1-(pyridin-2-yl)ethanone

HRID 2178045Notes

Reaction equation

HRID 2178045 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9]CC)=O.[CH2:12]([Mg]Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+]>O1CCCC1>[C:13]1([CH2:12][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 17307Ethyl 2-pyridinecarboxylateHCID 25517Ammonium ChlorideHCID 178418336HCID 178418336, compound

Product 1

HCID 2560732-phenyl-1-(pyridin-2-yl)ethanoneYield 53.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of ethyl picolinate (1.0 g, 6.62 mmol) in anhydrous tetrahydrofuran (15 mL) was added benzylmagnesium chloride (3.64 mL, 7.28 mmol) at −78° C. The mixture was stirred at −78° C. for 5 h, and poured into saturated aqueous ammonium chloride solution (70 mL), and extracted with ethyl acetate (50 mL×2). The organic layer was washed with brine (80 mL), and dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1) to give Intermediate 27 (700 mg, yield 53.6%).

Workup

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe organic layer was washed with brine (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-2c512a9121404efbb1e2f886cf94125f
Source dataset
uspto-grants-2015_06
Patent number
US09067893B2

Reaction notes

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