Dimethylformamide → HCID 66651992, compound

Participants

Reaction Steps

Combine [2-(2-methoxy-phenyl)-cyclohexyl]-acetic acid (0.300 g, 1.21 mmol), oxalyl chloride (0.13 mL, 1.45 mmol), and dichloromethane (6.0 mL) and catalytic DMF (0.1 mL) at room temperature. After 1 hour at 0° C. added TiCl4 (0.33 mL, 3.0 mmol) and reaction gradually warmed to room temperature. After 3 hours, quenched reaction with 5N HCl and added ethyl acetate. Separate layers, wash with brine, and dry over anhydrous sodium sulfate. Concentrate and flash chromatograph using 0 to 20% ethyl acetate/hexanes eluent to yield the titled compound (0.198 g, 72%). TLC Rf=0.4 in 20% ethyl acetate/hexanes. 1H NMR (CDCl3): 7.6 (d, 1H, J=7.0 Hz), 7.3 (m, 1H), 7.0 (m, 1H), 3.8 (s, 3H), 3.2 (m, 1H), 2.9 (m, 1H), 2.4 (m, 2H), 1.9 (m, 1H), 1.6 (m, 7H).

Provenance & Evidence