Acetonitrile → 3-Hydroxy-3-phenylbutanenitrile

Temperature

-20 °C

Dry THF was cooled to −20° C. and 2.5 M n-Bull (100 mL, 0.25 mol) was added. A solution of CH3CN (11.25 g, 0.25 mol) in dry THF was added dropwise over 10 min. Then the mixture was stirred for 1 h at −20° C. and a solution of acetophenone (30 g, 0.25 mol) in THF was added dropwise over 10 min. The mixture was stirred at −20° C. for 15 min and warmed to rt over 15 min. Aq NH4Cl was added to quench the reaction. The solution was extract with EtOAc. The organic layer washed with brine, dried over anhydrous Na2SO4 and concentrated to give 3-hydroxy-3-phenylbutanenitrile (30 g, yield 75%). 1H NMR (CDCl3, 400 MHZ): δ=1.76 (s, 3H), 2.83 (s, 2H), 7.34 (m, 1H), 7.41 (m, 2H), 7.5 (m, 2H).

1. addition2.5 M n-Bull (100 mL, 0.25 mol) was added
2. stirringThe mixture was stirred at −20° C. for 15 min
3. temperaturewarmed to rt over 15 min
4. customto quench
5. customthe reaction
6. extractionThe solution was extract with EtOAc
7. washThe organic layer washed with brine
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated

ORD record

ord-098613622b004fab9581a9912188d006

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575156B2