Sodium Hydroxide → [Rac]-(2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid

Participants

Reaction Steps

0.322 g (0.62 mmol) of the above prepared (2-methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethylsulfanyl}-phenoxy)-acetic acid tert-butyl ester, containing some methyl ester, was dissolved in 3.8 ml of THF/EtOH=1/1, treated with 1.87 ml (3 eq.) of 1N NaOH, and kept at ambient temperature for 2 h. The reaction mixture was then poured onto crashed ice/HCl dil., extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated to dryness to leave, after crystallization from AcOEt/hexane, 0.276 g of the title compound as off-white solid of mp. 115–117° C.

Provenance & Evidence