Acetonitrile → (3RS)-3-(3,4-dichlorophenyl)-3-hydroxy-4-methoxybutanenitrile

To a solution of 1.6 M n-butyllithium/hexane solution (20 ml) in THF (50 mL) was added dropwise a solution of acetonitrile (1.23 g) in THF (5 mL) at −78° C., and the mixture was stirred for 15 min, and at −40° C. for 15 min. A solution of 1-(3,4-dichlorophenyl)-2-methoxyethanone (5.00 g) in THF (30 mL) was added dropwise at −78° C., and the mixture was gradually warmed with stirring to room temperature, and stirred for 20 min. The reaction mixture was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-100%)) to give the title compound (5.63 g).

1. waitat −40° C. for 15 min
2. temperaturethe mixture was gradually warmed
3. stirringwith stirring to room temperature
4. stirringstirred for 20 min
5. customThe reaction mixture was quenched with water
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customthe solvent was evaporated
10. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-100%))

ORD record

ord-997cf602467b42569cd073dd4c05fe46

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2