Sodium Hydroxide → 3-(1-Methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid

Participants

Reaction Steps

A solution of Methyl 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoate (Intermediate 2) (6.8 g, 17.08 mmol, 1 equiv.) in a mixture of THF and methanol (70 mL of 1:1 ratio) was treated with a solution of sodium hydroxide (2 g, 51.25 mmol, 3 equiv.) in water (50 mL) and the reaction mixture was stirred for 1 h. The resulting solution was concentrated in vacuo to remove THF and methanol, diluted with water (50 mL), extracted with EtOAc. The aqueous phase was cooled and acidified with 0.1 N HCl and extracted with DCM, combined organic extracts washed with brine, dried over Na2SO4 and concentrated in vacuo to give 3-(1-methoxypropan-2-yloxy)-5-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)benzoic acid (5.1 g) as white solid.

Provenance & Evidence