Ethyl bromoacetate → Ethyl 2-(2-oxopyridin-1-YL)acetate

HRID 2053607Notes

Reaction equation

HRID 2053607 reaction equation
[H-].[Na+].[NH:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[O:9].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1COCC1.CN1C(=O)N(C)CCC1>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=[O:9])[CH3:16]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 88712-PyridoneHCID 24758Sodium hydride

Product 1

HCID 9497629Ethyl 2-(2-oxopyridin-1-YL)acetateYield 76.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

To a suspension of 60% sodium hydride dispersion in mineral oil (220 mg, 5.5 mmol) in cold (0° C.) THF is added 2-pyridone (475 mg, 5.0 mmol) in THF (4 mL) and DMPU (2 mL) followed by ethyl bromoacetate (0.556 mL, 5.0 mmol), and the reaction is stirred at RT for 1 h. The reaction is quenched with water, and extracted with EtOAc. The organic layer is separated, evaporated, and the residue purified by chromatography on silica gel; elution with EtOAC:dichloromethane:heptane (50:30:20) gives 690 mg of the product 425. 1H NMR (CDCl3) δ 7.35 (m, 1H), 7.21 (d, 1H), 6.57 (d, 1H), 6.19 (t, 1H), 4.62 (s, 2H), 4.23 (q, 2H), 1.28 (t, 3H); MS: m/z 182 (M++1).

Workup

  1. customThe reaction is quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer is separated
  4. customevaporated
  5. customthe residue purified by chromatography on silica gel
  6. washelution with EtOAC

Sources & evidence

ORD record
ord-85c52524d0204443ac20b624a94d3759
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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