HCID 86057409, compound → HCID 59214204, compound

Participants

Reaction Steps

To a solution of 440 mg (1.81 mmol) of 5-formyl-2-(2,2,2-trifluoro-1-methylethoxy)benzonitrile (from Step A) in 20 mL of acetone at 0° C. was added dropwise a solution of Jones reagent, which was prepared by dissolving 0.27 g (2.71 mmol) of chromium (VI) oxide in 0.25 mL of concentrated sulfuric acid and diluted with 2 mL of water at 0° C. The reaction mixture was gradually warmed up to rt, stirred overnight, and concentrated. The residue was diluted with 20 mL of EtOAc and washed with brine (10 mL), H2O (3×10 mL), and brine (10 mL). The organic layer was dried over MgSO4 and concentrated to give 0.44 g of the title compound: 1H NMR (500 Mhz, CDCl3) δ 1.69 (d, J=6.4, 3H), 4.94 (m, 1H), 7.16 (d, J=9.1, 1H), 8.34 (dd, J=2.0, 6.9, 1H), 8.42 (d, J=2.1, 1H).

Provenance & Evidence