Ethanol → (4-Methyloxazol-5-yl)(phenyl)methanone

HRID 1289050Notes

Reaction equation

HRID 1289050 reaction equation
[C:1]1([Li])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CON(C)[C:11]([C:13]1[O:17][CH:16]=[N:15][C:14]=1[CH3:18])=[O:12].C(O)C.[Cl-].[Na+]>O1CCCC1>[C:1]1([C:11]([C:13]2[O:17][CH:16]=[N:15][C:14]=2[CH3:18])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 18925369N-Methoxy-N,4-dimethyloxazole-5-carboxamideHCID 178506676HCID 178506676, compound

Product 1

HCID 53876795(4-Methyloxazol-5-yl)(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

Phenyllithium (1.8M solution in cyclohexane-diethylether, 11.7ml) in dry tetrahydrofuran was stirred and cooled to -70° C. under an atmosphere of dry nitrogen and N-methoxy-N-methyl-4-methyl-5-oxazolecarboxamide (3.0g) in dry tetrahydrofuran was added dropwise. After 30 minutes the mixture was allowed to warm to room temperature. Ethanol (5ml) 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. 84-86° C. 1H Nmr (CDCl3) 2.59 (3H, s), 7.5-7.68 (3H, m) and 7.96-8.06) (3H, m) ppm.

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted with dichloromethane
  3. customthe material thus obtained
  4. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-3cabfcf4a5cc4b649c69305f11bd9a8b
Source dataset
uspto-grants-1998_05
Patent number
US05747515

Reaction notes

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