Methyl iodide → HCID 68181709, compound

Temperature

60 °C

To a solution of 1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone (1.00 g, 7.09 mmol) in dry THF (20 mL) under an atmosphere of nitrogen was introduced cesium carbonate (2.31 g, 7.09 mmol) and methyl iodide (5.03 g, 35.43 mmol). The reaction mixture was warmed to 60° C. for 16 hr, cooled to RT and the solids removed by filtration. The filtrate was re-treated with additional cesium carbonate (4.31 g, 13.23 mmol) and methyl iodide (9.59 g, 67.58 mmol) and warmed to 60° C. for 34 hr. After cooling to RT, the reaction mixture was filtered, concentrated in vacuo and the residue re-dissolved in EtOAc (50 mL). The EtOAc solution was washed with water (25 mL), brine (25 mL), dried (Na2SO4) and filtered. After concentrating the filtrate in vacuo, the residual oil was purified by silica gel flash column chromatography (95:5-50:50 gradient of heptane/EtOAc) to furnish the title compound as a colorless oil: 1H NMR (500 MHz, CDCl3) delta 2.66 (3H, s), 3.44 (3H, s), 4.59 (2H, s), 6.64 (1H, s).

1. temperaturecooled to RT
2. customthe solids removed by filtration
3. temperaturewarmed to 60° C. for 34 hr
4. temperatureAfter cooling to RT
5. filtrationthe reaction mixture was filtered
6. concentrationconcentrated in vacuo
7. dissolutionthe residue re-dissolved in EtOAc (50 mL)
8. washThe EtOAc solution was washed with water (25 mL), brine (25 mL)
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationAfter concentrating the filtrate in vacuo
12. customthe residual oil was purified by silica gel flash column chromatography (95:5-50:50 gradient of heptane/EtOAc)

ORD record

ord-235a119bddcc4ce7974b481f4ad4fcd7

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901313B2