Di-tert-butyl peroxide → HCID 178445807, compound

Temperature

50 °C

Di-tert-butyl peroxide (1.93 mL, 10.5 mmol) was added to a suspension of Selenium dioxide (2.68 g, 24.1 mmol) in 1,4-Dioxane (24.00 mL, 307.5 mmol). The mixture was stirred for 30 minutes, then 6-(trans-4-tert-Butyl-cyclohexyloxy)-2-methyl-quinoline (3.12 g, 10.5 mmol) was added as a solution in 1,4-Dioxane and the mixture was heated overnight at 50° C. The reaction mixture was then cooled to room temperature, diluted in chloroform and filtered through a pad of celite. The filtrate was washed with water. The layers were separated and the combined organic phase was dried over MgSO4, filtered, concentrated under reduced pressure, adsorbed onto silica gel and purified by flash chromatography (0-30% EtOAc in hexanes) to give the title compound as a pale yellow solid in 20% yield. ESI-MS (M+H+): 312.27.

1. temperatureThe reaction mixture was then cooled to room temperature
2. filtrationfiltered through a pad of celite
3. washThe filtrate was washed with water
4. customThe layers were separated
5. dry with materialthe combined organic phase was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. custompurified by flash chromatography (0-30% EtOAc in hexanes)

ORD record

ord-7578df9ad83d440fb7bd27f12fa4ff46

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09186367B2