Iodoethane → Ethyl 2-ethoxypyridine-3-carboxylate

HRID 2407768Notes

Reaction equation

HRID 2407768 reaction equation
[CH2:1]([O:3][C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](I)[CH3:20]>CN(C)C=O>[CH2:1]([O:3][C:4]1[N:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([O:8][CH2:19][CH3:20])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 27363452-Ethoxynicotinic Acid

Product 1

HCID 12326832Ethyl 2-ethoxypyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of the compound prepared in Example 284 (1.3 g) and cesium carbonate (2.53 g) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 2 hours and then treated with ethyl iodide (0.62 mL) at room temperature, and stirring continued for 18 hours. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate and saturated aqueous solution of sodium bicarbonate. The combined organic extracts were washed with brine, dried and evaporated in vacuo to a yellow oil and purified by column chromatography on silica gel (10-50% ethyl acetate in hexane) to obtain the title compound (0.904 g) having the following physical data.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue partitioned between ethyl acetate and saturated aqueous solution of sodium bicarbonate
  5. washThe combined organic extracts were washed with brine
  6. customdried
  7. customevaporated in vacuo to a yellow oil
  8. custompurified by column chromatography on silica gel (10-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-1591268c5cd94d0f9de331cfe57d73cd
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…