Ethanol → Ethyl 5-ethoxypyridine-2-carboxylate

HRID 1478103Notes

Reaction equation

HRID 1478103 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1.[Na].[CH3:14][CH2:15][OH:16]>>[CH2:15]([O:16][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:6][CH:7]=1)[CH3:14]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 5360545SodiumHCID 12686158Ethyl 5-bromopicolinate

Product 1

HCID 67958698Ethyl 5-ethoxypyridine-2-carboxylate

Procedure

To a solution of ethyl 5-bromopyridine-2-carboxylate 2 (1.5 g, 6.5 mmol) in 20 mL of EtOH was added a solution of sodium (0.18 g, 7.8 mmol) in 20 mL of EtOH. The mixture was stirred at reflux for 3 h. After removal of all solvent, the residue was purified by column (2:1 of hexane/ethyl acetate) to give ethyl 5-ethoxypyridine-2-carboxylate 3 as an oil. Yield: 0.26 g, 20%. 1HNMR (CDCl3) δ (ppm): 8.38 (d, 1H), 8.10 (d, 1H), 8.23 (d, 1H), 7.22 (dd, 1H), 4.45 (m, 2H), 4.25 (m, 1H), 1.40 (m, 6H).

Workup

  1. temperatureat reflux for 3 h
  2. customAfter removal of all solvent
  3. customthe residue was purified by column (2:1 of hexane/ethyl acetate)

Sources & evidence

ORD record
ord-763d2a9322e84f219203b8a6517f3cad
Source dataset
uspto-grants-2016_08
Patent number
US09403812B2

Reaction notes

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