Acetonitrile → (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-(4-methoxyphenoxy)butanenitrile

Temperature

-78 °C

To a mixed solution of acetonitrile (3.54 mL) and THF (30 mL) was added dropwise a solution of n-butyllithium in hexane (1.6 M, 42.1 ml), and the mixture was stirred at −78° C. for 30 min. To the reaction mixture was added dropwise a solution of 1-(3,4-dichlorophenyl)-2-(4-methoxyphenoxy)ethanone (14 g) in THF (45 mL), and the mixture was stirred at −78° C. for 10 min, and then stirred for 1 hr while warming to room temperature. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The obtained extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (11.73 g).

1. stirringthe mixture was stirred at −78° C. for 10 min
2. stirringstirred for 1 hr
3. temperaturewhile warming to room temperature
4. extractionthe mixture was extracted with ethyl acetate
5. extractionThe obtained extract
6. washwas washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-6bb0851c74b34c8f89cec6e7c4f44b9e

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2