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

HRID 18816Notes

Reaction equation

HRID 18816 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-f9155f309e3a4569940f0a570f3f1469
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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