Sodium Hydroxide → HCID 57435135, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[2-(3-methoxy-phenyl)-ethyl]-5-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (127) in EtOH, 3 equiv of NaOH aq (3 M) was added then the mixture was heated at 80° C. for 1 hour. When the reaction is judged complete, the solvent was removed under vacuum, H2O was added and an equal volume of Et2O was added. The organic layer was removed then the aqueous layer was made acidic with HCl (1M). If the product precipitated out at this point, it was filtered off, washed with H2O, and dried to obtain pure desired product. If the product didn't crash out when the aqueous layer is made acidic, Et2O was added, and the organic layer was removed (2×). The organic layer was dried with Na2SO4, filtered, and concentrated to obtain desired product. Purification: Extraction. Amount: 37 mg. 1H (CDCl3, 400 MHz): δ 8.90 (NH, broad s), 7.19 (1H, dd), 6.88 (1H, s), 6.75 (2H, m), 6.94 (1H, s), 3.78 (3H, s), 2.80 (2H, dd), 2.68 (2H, dd), 2.08 (3H, s) ppm. 13C (CDCl3, 100 MHz): δ 165.5, 159.6, 143.5, 132.3, 129.3, 122.6, 121.0, 118.7, 117.8, 114.2, 111.2, 55.2, 37.3, 27.8, 11.3 ppm. HPLC (20 min): 91.6%. LC/MS: 97%.

Provenance & Evidence