Diethyl Carbonate → HCID 11310281, compound

Temperature

40 °C

To a solution of sodium hydride (4.2 g, 177.7 mmol) in THF was added 4-fluoro phenyl acetonitrile (10 g, 74.0 mmol) at −10° C. The reaction mixture was stirred for 15 min at the same temperature. Diethyl carbonate (10.5 g, 88.0 mmol) was added to the reaction mixture and the reaction mixture was allowed to come to room temperature and heated to 40° C. (Caution: Reaction will start suddenly and exothermic). The heating path was removed immediately once the reaction was started and the reaction mixture was cooled under ice/acetone. The solution was allowed to come to room temperature and stirred for 1 h. The reaction mass was cooled to 0° C. and quenched with aqueous saturated ammonium chloride and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with water (50 mL), brine solution (50 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure to give ethyl 2-cyano-2-(4-fluorophenyl)acetate as crude compound as crude compound (10 g). The crude compound was taken to the next step without further purification. LC-MS (M−H)+=206.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.44 (2H, m), 7.11 (2H, m), 4.69 (1H, s), 4.27-4.22 (2H, q, J=7.2 Hz). 1.26 (3H, m)

1. customto come to room temperature
2. customReaction
3. customThe heating path was removed immediately once the reaction
4. temperaturethe reaction mixture was cooled under ice/acetone
5. customto come to room temperature
6. stirringstirred for 1 h
7. temperatureThe reaction mass was cooled to 0° C.
8. customquenched with aqueous saturated ammonium chloride
9. extractionextracted with ethyl acetate (50 mL×3)
10. washThe combined organic layer was washed with water (50 mL), brine solution (50 mL)
11. dry with materialdried over anhydrous Na2SO4
12. customevaporated under reduced pressure

ORD record

ord-144e952bb59147bdbf8832dad72fd5b1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710061B2