5-Phenyl-3-isoxazolecarboxylic acid → Methyl 5-phenyl-1,2-oxazole-3-carboxylate

HRID 1804475Notes

Reaction equation

HRID 1804475 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([OH:14])=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:16]>C1(C)C=CC=CC=1.CO>[C:1]1([C:7]2[O:11][N:10]=[C:9]([C:12]([O:14][CH3:16])=[O:13])[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 1519165-Phenyl-3-isoxazolecarboxylic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 905953Methyl 5-phenyl-1,2-oxazole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-phenylisoxazole-3-carboxylic acid (0.86 g, 4.55 mmol) in toluene (15.0 mL) and methanol (3 mL) was added a 2M solution of TMS-diazomethane in hexanes (3.1 mL, 6.14 mmol) dropwise at room temperature. The reaction mixture was stirred for 30 minutes and concentrated. The residue was dispersed in methanol (3 mL), stirred for 5 minutes, and filtered to give methyl 5-phenylisoxazole-3-carboxylate (897 mg). The compound had an HPLC ret. time=2.67 min.: YMC S5 COMBISCREEN® 4.6×50 mm; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.2% H3PO4; Solvent B=90% MeOH−10% water−0.2% H3PO4; Start % B=0; Final % B=100. LC-MS: M+1=204+.

Workup

  1. concentrationconcentrated
  2. additionThe residue was dispersed in methanol (3 mL)
  3. stirringstirred for 5 minutes
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ad08a872416747bd9ef2e48dd14d8e2a
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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