2,6-Dimethoxybenzaldehyde → Ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate

Participants

Reaction Steps

A solution of commercially available (4-(trifluoromethoxy)phenyl)methanamine (11.858 g; 60.17 mmol) and commercially available 2,6-dimethoxybenzaldehyde (10.000 g; 60.17 mmol) in anh. EtOH (160 ml) was treated with diethyl oxalacetate sodium salt (13.312 g; 60.17 mmol). The resulting mixture was then refluxed, under nitrogen, for 8 h. After cooling to rt, the reaction mixture was concentrated to dryness under reduced pressure. DCM was added and the resulting heterogeneous mixture was washed with 1 M aq. HCl (2×), and with brine. The separated organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM to DCM/MeOH=30/1) afforded ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-3-carboxylate as an orange oil. LC-MS (conditions A): tR=0.89 min.; [M+H]+: 481.92 g/mol.

Provenance & Evidence