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0 °C

4-(Chloromethyl)benzoyl chloride (105 mg, 0.558 mmol) was added to a stirred solution of 2-dimethylamino-6-methoxybenzo[b]thiophene (105 mg, 0.507 mmol) in chlorobenzene (1 mL) under nitrogen. The resultant mixture was heated in an oil bath at 110° C. for 2.5 h. The mixture was cooled to 0° C., treated with pyrrolidine (5 mL), then allowed to stir at room temperature for 2 h. After dilution with THF (20 mL), the mixture was washed with saturated aqueous NaHCO3 (5 mL). The organic layer was dried over MgSO4, filtered, concentrated, and chromatographed on silica [gradient 20-40% EtOAc in hexanes, then 0-10% EtOH/Et3N (2/1) in THF/hexanes (1/1)] to give 148 mg (74%) of the ketone as a foam.

1. washAfter dilution with THF (20 mL), the mixture was washed with saturated aqueous NaHCO3 (5 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customchromatographed on silica [gradient 20-40% EtOAc in hexanes