HCID 86688427, compound → HCID 86688426, compound

Temperature

0 °C

To a stirred solution of the crude (S)—N-(4-chloro-2-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide (26.8 g, 86.0 mmol) in dichloromethane (290 mL) at −48° C. was added a solution of methyl magnesium bromide (3.0 M in diethyl ether, 63.0 mL, 189.0 mmol) dropwise. The reaction was stirred below −40° C. for 18 h, and the reaction was slowly warmed to 0° C. and quenched with 50% saturated aqueous ammonium chloride solution (100 mL). The phases were separated, and the organic layer was washed with deionized water (50 mL). The aqueous layer was further extracted with ethyl acetate (2×50 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by flash chromatography (SiO2, 50% ethyl acetate in hexanes) to afford the desired product (14.6 g, 44.5 mmol, 52%).

1. customquenched with 50% saturated aqueous ammonium chloride solution (100 mL)
2. customThe phases were separated
3. washthe organic layer was washed with deionized water (50 mL)
4. extractionThe aqueous layer was further extracted with ethyl acetate (2×50 mL)
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe crude material was purified by flash chromatography (SiO2, 50% ethyl acetate in hexanes)

ORD record

ord-769d3007b0874727b4e0ee4fe1d5f611

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150550B2