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-1ed159fb57024331834943c5f2027630

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685959B2