Sodium Bicarbonate → 4-Methyl-5-propionyloxazole

HRID 975038

Reaction equation

HRID 975038 reaction equation
CON(C)[C:4]([C:6]1[O:10][CH:9]=[N:8][C:7]=1[CH3:11])=[O:5].[CH2:13]([Mg]Br)[CH3:14].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:11][C:7]1[N:8]=[CH:9][O:10][C:6]=1[C:4](=[O:5])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamideHCID 178418443HCID 178418443, compound

Product 1

HCID 189363294-Methyl-5-propionyloxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (5 g) in dry tetrahydrofuran at -40° C. was stirred under a nitrogen atmosphere and ethylmagnesium bromide (1M solution in tetrahydrofuran, 35 ml) was added dropwise. After 30 minutes the mixture was allowed to warm to room temperature and then stirred for a further 1 hour. Aqueous sodium hydrogen carbonate was added, the organic layer was separated and the aqueous layer was extracted with diethylether. The material thus obtained was purified by flash chromatography to yield a pale yellow liquid which solidified on cooling.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with diethylether
  3. customThe material thus obtained
  4. customwas purified by flash chromatography
  5. customto yield a pale yellow liquid which
  6. temperatureon cooling

Sources & evidence

ORD record
ord-14f1b749a0f249299ac8e0e73b1a91bb
Source dataset
uspto-grants-1997_03
Patent number
US05607956

Linked notes

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