2-Methoxybenzaldehyde → 5-(2-Methoxyphenyl)-1,3-oxazole

HRID 1581787Notes

Reaction equation

HRID 1581787 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].S([CH2:21][N+:22]#[C-:23])(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]1[O:6][CH:23]=[N:22][CH:21]=1

Participants

5

Reactant 3

HCID 86582-MethoxybenzaldehydeHCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 167406765-(2-Methoxyphenyl)-1,3-oxazoleYield 70.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-methoxybenzaldehyde (10.0 g, 73.4 mmol), tosylmethylisocyanide (14.34 g, 73.4 mmol) and potassium carbonate (10.14 g, 73.4 mmol) in 220 ml methanol is heated at reflux for 6 hours. The solvent is removed under reduced pressure and the residue poured into ice-water (800 ml). The precipitate is collected by filtration, washed with water, and dried in vacuo to give 9.05 g of 5-(2-methoxyphenyl)oxazole (70%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. customThe solvent is removed under reduced pressure
  4. additionthe residue poured into ice-water (800 ml)
  5. filtrationThe precipitate is collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-b811ba8842d64631a744eb5d9830d8f1
Source dataset
uspto-grants-2004_05
Patent number
US06730792B2

Reaction notes

Loading…