Benzaldehyde → HCID 21825613, compound

4-methyl-nicotinonitrile (2.0 g, 16.93 mmol) was dissolved in20 mL of anhydrous THF(20 mL), added with LHMDS (1M solution in THF, 34 mL, 33.86 mmol) at −78° C. under the nitrogen atmosphere and then stirred for about 1 hour at the same temperature. The mixture was dropwisely added with benzaldehyde (2.1 mL, 20.32 mmol) and stirred at −50° C. for about 1 hour. The mixture, while being stirred at 0° C., added with 30 mL of saturated solution of ammonium chloride and 50 ML of distilled water, and then extracted twice with 100 ML of EtOAc. The resulting organic layer was washed with a saturated solution of sodium chloride, dried with anhydrous sodium sulfate, filtered and concentrated. A silica gel column chromatography (2% MeOH/MC) was performed on the resulting residue and obtained 3.46 g (91%) of 4-(2-hydroxy-2-phenyl-ethyl)-nicotinonitrile in pale yellow solid.

1. stirringstirred at −50° C. for about 1 hour
2. stirringThe mixture, while being stirred at 0° C.
3. extractionextracted twice with 100 ML of EtOAc
4. washThe resulting organic layer was washed with a saturated solution of sodium chloride
5. dry with materialdried with anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-b20619d637bf4c9f8a0319fa85a3eed3

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07601736B2