Potassium Carbonate → tert-butyl 2-(2-oxopyridin-1(2H)-yl)propanoate

HRID 243695Notes

Reaction equation

HRID 243695 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:14]([O:18][C:19](=[O:23])[CH:20](Br)[CH3:21])([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C.O>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[CH:20]([CH3:21])[C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 545327tert-Butyl 2-bromopropanoateHCID 178516071HCID 178516071, compound

Product 1

HCID 57907642tert-butyl 2-(2-oxopyridin-1(2H)-yl)propanoateYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 9.5 g (0.10 mol) of 2-hydroxypyridine in 250 mL of DMF was added 16.6 g (0.120 mol) of potassium carbonate followed by 25.0 g (0.120 mol) of 2-bromopropionic acid tert-butyl ester. The resulting mixture was stirred at ambient temperature for 7 h then diluted with 1 L of water. The aqueous phase was extracted with ethyl acetate (3×200 mL) and the combined organics were washed with water (2×100 mL), brine (100 mL), dried over magnesium sulfate, filtered and evaporated in vacuo. The crude residue was purified by silica gel chromatography eluting with 25% ethyl acetate in hexanes to afford the title compound as a clear gum 16 g (72%). LC-MS: m/z (ES) 224 (MH)+

Workup

  1. extractionThe aqueous phase was extracted with ethyl acetate (3×200 mL)
  2. washthe combined organics were washed with water (2×100 mL), brine (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude residue was purified by silica gel chromatography
  7. washeluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-840d93c384914fb2993f76533a242157
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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