Sodium Hydroxide → 2-(4-(5-Ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyacetic acid

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Reaction Conditions

Reaction Steps

To a solution of 2,2,2-trichloro-1-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)ethanol (2.0 g, 6.25 mmol) in anhydr 1,4-dioxane (12.5 mL) and anhydr MeOH (15 mL) was added a solution of NaOH (1.25 g, 31.3 mmol) in anhydr MeOH (15 mL). After stirring for 4 hrs at 55° C., the mixture was cooled to room temperature and concentrated in vacuo. The residue was neutralized with saturated aqueous NH4Cl, acidified carefully with 1 M HCl and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo. The residue was triturated with Et2O to give 2-(4-(5-ethyl-1,3,4-oxadiazol-2-yl)phenyl)-2-methoxyacetic acid as an off-white solid (1.2 g, 73% yield).

Provenance & Evidence