Sodium Chloride → 3-Furyl 4-Methyl-5-oxazolyl Ketone

HRID 2795

Reaction equation

HRID 2795 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.CON(C)[C:15]([C:17]1[O:21][CH:20]=[N:19][C:18]=1[CH3:22])=[O:16].[Cl-].[Na+]>C(OCC)C.C(O)C>[CH3:22][C:18]1[N:19]=[CH:20][O:21][C:17]=1[C:15]([C:2]1[CH:6]=[CH:5][O:4][CH:3]=1)=[O:16]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 891643-BromofuranHCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamideHCID 178418339Butyllithium

Product 1

HCID 189363073-Furyl 4-Methyl-5-oxazolyl Ketone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-70 °C

Procedure

3-Bromofuran (2.5 g) in dry diethylether was stirred and cooled to -70° C. under an atmosphere of dry nitrogen and n-butyllithium (2.5M solution in hexane, 6.8 ml) was added dropwise. After 30 minutes, N-methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (2.89 g) in dry diethylether was added dropwise. After a further 30 minutes the mixture was allowed to warm to room temperature. Ethanol (5 ml) was added followed by saturated aqueous sodium chloride. The mixture was extracted with dichloromethane and the material thus obtained was purified by flash chromatography to give the title compound. M.p. 82°-83.5° C.

Workup

  1. waitAfter a further 30 minutes the mixture was allowed
  2. temperatureto warm to room temperature
  3. extractionThe mixture was extracted with dichloromethane
  4. customthe material thus obtained
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-69d90fe1ebe346e2ad0d74e44a53c346
Source dataset
uspto-grants-1998_03
Patent number
US05731335

Linked notes

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