Benzaldehyde → 5-Phenyl oxazole

HRID 1457207Notes

Reaction equation

HRID 1457207 reaction equation
S([CH2:11][N+:12]#[C-:13])(C1C=CC(C)=CC=1)(=O)=O.[CH:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:15]1([C:14]2[O:21][CH:13]=[N:12][CH:11]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 5893115-Phenyl oxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tosylmethyl isocyanide (5.86 g, 30 mmol), benzaldehyde (3.18 g, 30 mmol) and K2CO3 (6.22 g, 45 mmol) in 60 ml MeOH was refluxed for 2 hr and concentrated. 250 ml EtOAc was added and the mixture was washed with H2O, brine, dried and concentrated. The residue was chromatographed on silica gel using 15:1 hexane/EtOAc to afford the title compound of this step (2.5 g, 57%) as a white solid.

Workup

  1. temperaturewas refluxed for 2 hr
  2. concentrationconcentrated
  3. addition250 ml EtOAc was added
  4. washthe mixture was washed with H2O, brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel using 15:1 hexane/EtOAc

Sources & evidence

ORD record
ord-feb70c9b854b461ab3b6fa7cdcdc953e
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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