Diethyl Carbonate → HCID 57654488, compound

HRID 1896286Notes

Reaction equation

HRID 1896286 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[H-].[K+].[C:11](=[O:18])([O:15][CH2:16][CH3:17])OCC>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]([C:11]([O:15][CH2:16][CH3:17])=[O:18])[C:11]([O:15][CH2:16][CH3:17])=[O:18])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 7766Diethyl CarbonateHCID 772482-Chloro-4-methylpyridineHCID 82127Potassium hydride

Product 1

HCID 57654488HCID 57654488, compoundYield 36%

Procedure

2-Chloro-4-picoline was added to a solution of potassium hydride (1.80 g, 15.8 mmol) in diethyl carbonate (10 ml) at 0° C. The reaction mixture was allowed to attain room temperature and stirred overnight. The reaction mixture was quenched with saturated ammonium chloride (15 ml) and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuum to afford the crude product. Purification by column chromatography over silica gel (60-120 mesh) using 8% ethyl acetate in petroleum ether as eluent afforded 750 mg (36%) of diethyl 2-(2-chloropyridin-4-yl)malonate as colorless liquid.

Workup

  1. customto attain room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride (15 ml)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customto afford the crude product
  8. customPurification by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-6fcdbbb266a447e6b4af76f4cb149a28
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

Loading…