Diethyl Malonate → Diethyl [(2-methyl-4-phenyl-1,3-oxazol-5-yl)methyl]propanedioate

HRID 1982422Notes

Reaction equation

HRID 1982422 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][C:16]1[O:20][C:19]([CH3:21])=[N:18][C:17]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.O>[CH3:21][C:19]1[O:20][C:16]([CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[C:17]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:18]=1

Participants

6

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 132932915-(Bromomethyl)-2-methyl-4-phenyl-1,3-oxazole

Product 1

HCID 13646801Diethyl [(2-methyl-4-phenyl-1,3-oxazol-5-yl)methyl]propanedioateYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

60% Sodium hydride in oil (1.48 g) was added portionwise to a solution of diethyl malonate (11.7 g) in N,N-dimethylformamide (50 ml) and the mixture was stirred for 10 minutes. A solution of 5-bromomethyl-2-methyl-4-phenyloxazole (9.2 g) in N,N-dimethylformamide (20 ml) was added dropwise under ice-cooling. The mixture was stirred under ice-cooling for 30 minutes, diluted with water, and extracted with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous sodium sulfate. The solvent was then distilled off and the residue was purified by silica gel chromatography [silica gel: 120 g; eluent: hexane-ethyl ether (3:2)] to give an oil (8.0 g) of diethyl 2-(2-methyl-4-phenyl-5-oxazolylmethyl)malonate.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 30 minutes
  4. extractionextracted with ethyl ether
  5. washThe ethyl ether layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was then distilled off
  8. customthe residue was purified by silica gel chromatography [silica gel: 120 g; eluent: hexane-ethyl ether (3:2)]

Sources & evidence

ORD record
ord-c61749d4317c40b98b21f53403bb6a5b
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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