2-Iodoxybenzoic acid → 3-Phenyl-1,2-oxazole-5-carbaldehyde

HRID 2407658Notes

Reaction equation

HRID 2407658 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([CH2:12][OH:13])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I(C1C=CC=CC=1C(O)=O)(=O)=O>C(OCC)(=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=[O:13])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 1087942-Iodoxybenzoic acidHCID 2763417(3-Phenyl-5-isoxazolyl)methanol

Product 1

HCID 113672673-Phenyl-1,2-oxazole-5-carbaldehydeYield 83.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3-phenylisoxazol-5-yl) methanol (10.0 g) and 2-iodoxybenzoic acid (24.0 g) in ethyl acetate (350 mL) was refluxed overnight. The mixture was cooled to room temperature, filtered and concentrated. The resulting solids were triturated (hexane:diethyl ether=1:1) to obtain the title compound (8.22 g) having the following physical data.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe resulting solids were triturated (hexane:diethyl ether=1:1)

Sources & evidence

ORD record
ord-be646b9221064e3ab29bc65e80556eed
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…