tert-Butyl hydroperoxide → HCID 86628362, compound

Temperature

0 °C

A solution of methyl 2-[6-fluoro-3-(methyloxy)-5-quinoxalinyl]-2-propenoate (5.45 g, 0.02 mol) (for a preparation, see Example 1(l)) in THF (150 ml) was cooled to 0° C. A 6M solution tert-butyl hydrogen peroxide in nonane (5.2 mL, 0.03 mol) was added dropwise followed by a 1M solution of potassium tert-butoxide (10.39 mL, 0.01 mol). During the addition the temperature was kept at 0° C. The reaction mixture was kept at 0° C. for 16 hours. Another 0.5 equivalent of the 1M solution of potassium tert-butoxide (10.39 mL, 0.01 mol) was added at 0° C. and the reaction mixture was kept for a further 2 hours. The reaction was quenched by addition of a 1M solution of HCl in methanol (20 mL). The reaction mixture was evaporated to dryness. The residue was partially dissolved in methanol. The organic layer was dried over magnesium sulphate, filtered, evaporated under vacuum and chromatographed on silica (required repeated chromatography), eluting with a 0-30% methanol in dichloromethane gradient to afford the product as a white solid (3.22 g, 59%)

1. additionDuring the addition the temperature
2. customwas kept at 0° C
3. waitthe reaction mixture was kept for a further 2 hours
4. customThe reaction was quenched by addition of a 1M solution of HCl in methanol (20 mL)
5. customThe reaction mixture was evaporated to dryness
6. dissolutionThe residue was partially dissolved in methanol
7. dry with materialThe organic layer was dried over magnesium sulphate
8. filtrationfiltered
9. customevaporated under vacuum
10. customchromatographed on silica (required repeated chromatography)
11. washeluting with a 0-30% methanol in dichloromethane gradient

ORD record

ord-ed30cb751a6b43e78ceafcab6443f282

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709483B2