Sodium Hydroxide → HCID 86696595, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of ethyl[2-oxo-1-propyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoate (0.071 g; 0.152 mmol) in a mixture of methanol and ethanol (2:1) (4.5 mL) was added a 5% sodium hydroxide solution (3.66 mL; 4.57 mmol) and the reaction mixture was heated to 90° C. for 7 h. The organic volatiles were removed under reduced pressure and the remaining basic solution was acidified to pH 2 with a 1N hydrochloric acid solution. The aqueous layer was extracted with ethyl acetate and the organics were combined, dried over sodium sulfate, concentrated under reduced pressure. Purification by preparative HPLC (method 2) furnished 0.015 g (22.7%) of 2-[2-oxo-1-propyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]pentanoic acid as a white solid. ESI/APCI(+): 438 (M+H).

Provenance & Evidence