Dimethylformamide → HCID 18399658, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylformamide (0.8 ml, 10 mmol) was added dropwise to a solution of phosphorus tribromide (0.8 ml, 8.5 mmol) in dry chloroform (20 ml) at 0° C. The mixture was stirred at 0° C. for 1 h to give pale yellow suspension. A solution of compound 6,7-methylenedioxy-2-tetralone (500 mg, 2.6 mmol) in dry chloroform(20 ml) was added to the yellow suspension and the mixture was heated at reflux for 1 h. The reaction mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added dropwise until no effervescence was obtained. The resulting mixture was extracted with dichloromethane, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed over 100 g of silica gel using 3:1 mixture respectively of hexanes and ethyl acetate to give the aldehyde in 60% yield; 1H NMR(CDCl3) δ2.80(2H, t, J=7.8), 2.98(2H, t, J=7.8), 5.93(2H, s), 6.64(1H, s), 7.57(1H, s), 10.28(1H, s); 13C NMR(CDCl3) δ29.3, 30.4, 101.6, 107.3,108.6, 124.0, 129.7, 132.7, 114.0, 146.7, 147.7, 193.2.

Provenance & Evidence