Diethyl Ether → HCID 12034489, compound

Temperature

0 °C

A solution of MeMgBr in ether (50.0 mL, 3.0 M, 0.15 mol) was added to a solution of diisopropylamine (16.17 g, 0.16 mol) in toluene (250 mL) at 50° C. The mixture was stirred for 1.5 h and a white precipitate formed. Next, the mixture was cooled to 0° C. and benzonitrile (15.4 g, 0.15 mol) was added. The mixture was allowed to warm to room temperature and stirred for 16 h subsequently. The conversion, determined by GC, appeared to be 90%. The mixture was quenched with water (100 mL). The organic phase was separated from the aqueous phase and the latter was extracted with diethylether (50 mL) twice. The combined organic phases were dried over Na2SO4, filtered and the solvents were removed under reduced pressure. The crude product was distilled at 145° C. at reduced pressure (0.52 mbar) resulting in 15.3 g (50%) of pure product. The ligand was characterized by 1H NMR (300 MHz) (CDCl3) δ (ppm): 7.2 (m, 5H), 5.7 (bs, 1H), 3.5 (p, 2H), 1.2 (d, 12H) and by 13C-NMR (75.5 MHz) (CDCl3) δ (ppm) 168.4, 141.8, 128.8, 128.5, 126.2, 48.6, 21.2.

1. customa white precipitate formed
2. temperatureto warm to room temperature
3. stirringstirred for 16 h subsequently
4. customThe mixture was quenched with water (100 mL)
5. customThe organic phase was separated from the aqueous phase
6. extractionthe latter was extracted with diethylether (50 mL) twice
7. dry with materialThe combined organic phases were dried over Na2SO4
8. filtrationfiltered
9. customthe solvents were removed under reduced pressure
10. distillationThe crude product was distilled at 145° C. at reduced pressure (0.52 mbar)

ORD record

ord-b3bf3a6cbe8243999f142a4b91f58c83

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956140B2