Potassium Carbonate → 5-(5-Oxazolyl)-2-furanmethanol

300 mg of 5-formylfurfuryl alcohol see Japanese Laid-Open Patent Publication No. 154758/1979 was dissolved in 10 ml of methanol, and 502 mg of p-toluenesulfonylmethyl isocyanide and 329 mg of potassium carbonate were added. The mixture was heated under reflux for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a mixture of water and ethyl acetate. The organic layer was separated, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography Wakogel C-200, 45 g; eluting solvent: hexane/ethyl acetate=3/2→1/1] to give 260 mg (yield 66%) of the captioned compound as a pale yellow crystalline powder.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 1 hour
3. concentrationThe reaction mixture was concentrated under reduced pressure
4. dissolutionthe residue was dissolved in a mixture of water and ethyl acetate
5. customThe organic layer was separated
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe desiccant was separated by filtration
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography Wakogel C-200, 45 g

ORD record

ord-a35c3c14f4af44af9f950a744a8ed223

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05234946