Sodium hydride → Ethyl acetate hexane

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (100 mg, 5 mmol) was added to a stirred solution of 3,4-methylenedioxyphenol (0.607 g, 4.5 mmol) in DMF (dry, 5 mL) at 0° C. under a nitrogen atmosphere with stirring. The reaction mixture was permitted to attain room temperature and stirring continued for 1 hr. The reaction mixture was cooled to 0° C. and N-[(2-bromomethyl)thiophene-3-sulfonyl]pyrrole was added. Stirring was continued at ambient temperature for 16 hr. The reaction mixture was diluted with water (100 mL), extracted with ethyl acetate (2×50 mL) and washed with 1 N NaOH (2×25 mL) to remove phenol derivative. The mixture was dried over MgSO4 and concentrated resulting in N-{2-[(3,4-methylenedioxy)phenoxymethyl]thiophene-3-sulfonyl}pyrrole, which was recrystallized using hexane/EtOAc (1.0 g, 92% yield).

Provenance & Evidence