2-(2-pyrrolidin-1-ylethoxy)benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-(2-chloroethoxy)benzaldehyde (40; 2.5 g, 13.5 mmol), pyrrolidine (172; 1.9 g, 26.8 mmol), K2CO3 (3.8 g, 27.2 mmol) and NaI (0.6 g, 4.2 mmol) in DMF (50 mL) was stirred at 80° C. for 12 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed brine (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (dichloromethane:methanol=100:1) to give 2-(2-(pyrrolidin-1-yl)ethoxy)benzaldehyde 41 (1.63 g, 7.43 mmol, 55%) as a pale yellow solid. the mixture was extracted with ethyl acetate (3×150 mL) The combined organic layers were washed brine (3×50 mL) dried (Na2SO4) concentrated under reduced pressure The resulting residue was purified by chromatography (dichloromethane:methanol=100:1)