Vilsmeier-Haack aroylation of 1-BenzoylmorpholineVilsmeier-Haack aroylation of 1-Benzoylmorpholine
SyntheticPage 651
Published Jul 24, 2013
1-Benzoylmorpholine (2.38 g, 12.5 mmol) and freshly distilled POCl3 (2.5 mL, 26.8 mmol) were mixed under an atmosphere of dinitrogen. The suspension was heated to 35 ºC until the solids were dissolved. The reaction was stirred at ambient temperature for another 5 h before pyrrole (0.55 g, 8.2 mmol) in dry 1,2- dichloroethene (ca. 50 mL) was added quickly. This was stirred overnight. Saturated Na2CO3 was slowly added to the reaction solution until the aqueous layer reached pH ca. 8. The separated organic layer was collected and the aqueous solution further extracted to chloroform (4 x 25 mL). Organic solvents were combined and washed with brine (2 x 20 mL) and dried over Na2SO4. The solvents were removed under reduced pressure to leave an off-white product. (1.25 g, 89 %).