Hydrochloric Acid → HCID 59516813, compound

Temperature

-74 °C

To a solution of 665 mg of 4-fluoro-7-methoxy-2,3-dihydrobenzofuran and 740 mg of N,N,N′,N′,N″-pentamethyldiethylenetriamine in 15 ml of THF there was added dropwise 1.66 ml of n-butyllithium (2.55 M, hexane solution) at −74° C. The mixture was stirred at −74° C. for 1 hour, and then 500 μl of N-formylmorpholine was added. After further stirring at room temperature for 1 hour, 1N hydrochloric acid was added to the reaction mixture while cooling on ice, and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (321 mg) as an oil.

1. stirringAfter further stirring at room temperature for 1 hour
2. temperaturewhile cooling on ice
3. extractionthe mixture was extracted with ethyl acetate
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationThe desiccating agent was filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

ORD record

ord-a2627d3c427d42ebbba3774b3df8c806

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07928228B2