Ammonium Chloride → HCID 86724257, compound

Temperature

-78 °C

To a solution of 6-bromo-4H-chromen-4-one (12 g, 53 mmol) in CH2Cl2 (24 mL) was added TMSOTf (12.5 mL, 69.18 mmol) at ambient temperature. After stirring for 1 hour, THF (210 mL) was added to the mixture at ambient temperature and cooled to −78° C. To the mixture was added n-propylmagnesium bromide (1.05M solution in THF, 66 mL, 69 mmol). After stirring for 1 hour at −78° C., 1M aqueous NH4Cl was added to the mixture. The mixture was warmed to ambient temperature and stirred overnight. The organic and the aqueous layers were separated, and the organic layer was dried over Na2SO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 10%) to afford 6-bromo-2-propyl-2,3-dihydro-4H-chromen-4-one (11.42 g).

1. stirringAfter stirring for 1 hour at −78° C.
2. temperatureThe mixture was warmed to ambient temperature
3. stirringstirred overnight
4. customThe organic and the aqueous layers were separated
5. dry with materialthe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated in vacuo
8. customThe residue was purified by silicagel column chromatography (EtOAc-hexane

ORD record

ord-c619f0cbaa8745e9ad5acab6db483c47

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08975415B2