Tetrahydrofuran → HCID 318403, compound

Participants

Reaction Steps

Iso-propyl magnesium chloride (2 M solution in THF; 3.0 mL; 6.0 mmol) was added to an ice-cooled solution of 4-iodobenzonitrile (1.2 g, 5.0 mmol) in anhydrous THF (10 mL). This solution was stirred at this temperature for 10 minutes and then added dropwise to a cooled (−78° C.) solution of N-2-dimethoxy-N-methylacetamide (0.998 g, 7.50 mmol) in anhydrous THF (5 mL). The reaction mixture was stirred at this temperature for 1 hour and then stirred at RT for 1 hour. The reaction mixture was then treated with 10% aqueous potassium hydrogen sulfate solution and extracted with DCM. The organic phase was passed through a hydrophobic frit and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with iso-hexane/EtOAc (3:2) to afford the title compound. 1H NMR (CDCl3, 400 MHz) δ 8.06-8.04 (m, 2H), 7.80-7.77 (m, 2H), 4.67 (s, 2H), 3.50 (s, 3H).

Provenance & Evidence