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

HRID 924950Notes

Reaction equation

HRID 924950 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-de54b72a9b68480d9561c1296b84746e
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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