Benzaldehyde → 5-Phenyl oxazole

HRID 868921Notes

Reaction equation

HRID 868921 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:9]([CH2:11]S(C1C=CC(C)=CC=1)(=O)=O)#[C-:10].C([O-])([O-])=O.[K+].[K+]>CO>[C:2]1([C:1]2[O:8][CH:11]=[N:9][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 5893115-Phenyl oxazoleYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of benzaldehyde (3 g, 28.3 mmol), 1-(isocyanomethylsulfonyl)-4-methylbenzene (5.5 g, 28.3 mmol) and K2CO3 (5.9 g, 42.5 mmol) in 60 mL methanol was refluxed for 2 h and then concentrated. 250 mL EtOAc was added and the mixture was washed with water and brine, dried, and concentrated to give 5-phenyl oxazole (3.4 g). MS (ESI) m/z 145 (M+H+).

Workup

  1. temperaturewas refluxed for 2 h
  2. concentrationconcentrated
  3. addition250 mL EtOAc was added
  4. washthe mixture was washed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b7765c3dcfaa4e14b2a990fe1a6021e7
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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