Diethyl Carbonate → 3-Methyl-2-pyridineacetic acid ethyl ester

HRID 1907672Notes

Reaction equation

HRID 1907672 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[C:2]=1[CH3:8].C([Li])CCC.[C:14](=O)([O:18]CC)[O:15][CH2:16][CH3:17].[Cl-].[NH4+]>O1CCCC1>[CH3:7][C:3]1[C:2]([CH2:8][C:14]([O:15][CH2:16][CH3:17])=[O:18])=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7766Diethyl CarbonateHCID 114202,3-LutidineHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 134006493-Methyl-2-pyridineacetic acid ethyl esterYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 10.72 g of 2,3-lutidine and 150 ml of tetrahydrofuran was added 63 ml of n-butyllithium (1.6 mol/L hexane solution) at room temperature. Into the mixture, a mixture of 11.81 g of diethyl carbonate and 50 ml of anhydrous tetrahydrofuran was added dropwise at −70° C. The mixture was heated up to room temperature. The reaction mixture was added to ice-cooled ammonium chloride aqueous solution, and extracted with tert-butyl methyl ether. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure. 16.16 g of the resultant residue was subjected to silica gel column chromatography, to obtain 6.31 g of ethyl (3-methyl-2-pyridyl)acetate.

Workup

  1. additionwas added dropwise at −70° C
  2. additionThe reaction mixture was added to ice-
  3. extractionextracted with tert-butyl methyl ether
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12a1837fab704cf0b72e0952ca902bb0
Source dataset
uspto-grants-2013_12
Patent number
US08598176B2

Reaction notes

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