Diethyl Carbonate → Ethyl 2-(5-methylpyridin-2-yl)acetate

HRID 481400Notes

Reaction equation

HRID 481400 reaction equation
[N:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[CH:3][C:2]=1[CH3:8].C([Li])CCC.[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17]>C1COCC1>[CH2:16]([O:15][C:14](=[O:18])[CH2:8][C:2]1[CH:3]=[CH:4][C:5]([CH3:7])=[CH:6][N:1]=1)[CH3:17]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 115262,5-DimethylpyridineHCID 178418339Butyllithium

Product 1

HCID 571749Ethyl 2-(5-methylpyridin-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 2,5-lutidine (540 mg, 5.05 mM) in 10 ml of THF at -10° C. was added 2.5M n-butyllithium solution (2.0 ml, 5.00 mM). The resulting mixture was stirred for 30 minutes while allowing the temperature to rise to 0° C. The reaction was cooled to -50° C. and diethyl carbonate (0.61 ml, 5.00 mM) was added and the reaction was warmed to room temperature and stirred for 2 hours. The reaction was quenched with saturated NH4Cl solution and extracted into EtOAc. The resulting organic layer was washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated to dryness. The residue was chromatographed on silica gel using 30% EtOAc/hexanes as the eluant to yield the title compound (43).

Workup

  1. customto rise to 0° C
  2. temperaturethe reaction was warmed to room temperature
  3. stirringstirred for 2 hours
  4. customThe reaction was quenched with saturated NH4Cl solution
  5. extractionextracted into EtOAc
  6. washThe resulting organic layer was washed with saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customThe residue was chromatographed on silica gel using 30% EtOAc/hexanes as the eluant

Sources & evidence

ORD record
ord-ee705517192e4ae799b75f59da1e8e86
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

Loading…