Sodium Hydroxide → 5,6,7,8-Tetrahydro-2-methyl-α-(1-methylethyl)-4-(4-methylphenyl)[1]benzothieno[2,3-b]pyridine-3-acetic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl [2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-3-methylbutanoate (0.109 g; 0.267 mmol) in methanol (2.7 mL) was added a solution of sodium hydroxide 5 N (0.53 mL) and the mixture was heated at 60° C. for 18 h. After cooling, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the mixture was acidified with HCl (1N) until pH 1. The organic layer was washed with brine, water, dried over magnesium sulphate and concentrated under reduced pressure. A purification by preparative TLC using a mixture ethyl acetate/heptane (1:1)+0.5% AcOH furnished 0.0013 g (12%) of the title compound as a light yellow solid.

Provenance & Evidence