Dimethylformamide → HCID 59888900, compound

Participants

Reaction Steps

6,7-Dihydrobenzo[b]thiophen-4(5H)-one (1.0 g, 6.6 mmol) in toluene (10 mL) was added drop-wise to NaH (60% dispersion in mineral oil, 1.32 g, 32.9 mmol) in toluene (5 mL). DMF (5 mL) was added and the reaction was stirred at room temperature for 1 hr. The mixture was cooled to 0° C., methyl iodide (4.67 g, 2.1 mL, 32.9 mmol) was added drop-wise and the solution was refluxed for 3 h. The mixture was cooled and carefully treated with iso-propanol. The product was extracted into diethyl ether (×3) and this was back extracted with water and saturated brine. The diethyl ether solution was dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified on silica gel using a gradient elution of 0-75% ethyl acetate in 40-60 petroleum ether to afford the title compound as a yellow oil (0.375 g, 32%).

Provenance & Evidence