Methoxymethyl-triphenylphosphonium chloride → HCID 86694455, compound

Temperature

-78 °C

In a 250 ml, round bottom flask, (methoxymethyl) (triphenyl)phosphonium chloride (1.3 g, 3.8 mmol) was dissolved in THF (20 mL). The solution was cooled to −78° C. To above solution was added n-butyl lithium (0.49 mL, 2.50 M in Hexane, 1.05 mmol) dropwise. Reaction color changed to orange. The mixture was cooled to −78° C. and to it was added 6-Fluoro-4-oxo-3,4-dihydro-2H-chromene-7-carbonitrile (100 mg, 0.52 mmol). The reaction was let warm to RT and stirred at RT for 18 hours. The reaction was then quenched with addition of saturated ammonium chloride (5 mL) and extracted with dichloromethane. The organic phase was washed with brine (5 mL), dried over anhydrous Na2SO4, filtered, concentrated and purified by flash column chromatography (hexane/EtOAc 0-50%). The desired product was obtained. LC-MS (IE, m/z): 220.3 [M+1]+.

1. customReaction color
2. temperatureThe mixture was cooled to −78° C. and to it
3. temperatureThe reaction was let warm to RT
4. customThe reaction was then quenched with addition of saturated ammonium chloride (5 mL)
5. extractionextracted with dichloromethane
6. washThe organic phase was washed with brine (5 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. custompurified by flash column chromatography (hexane/EtOAc 0-50%)

ORD record

ord-98e9c76743794ee9bcfccafc637ab29a

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073882B2