Triphenylphosphine → 4-[3-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-[1,2,4]oxadiazol-5-ylmethyl]-benzoic acid ethyl ester

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Reaction Steps

Add polymer support PPh3 (287 mg, 0.86 mmol to a solution of 4-(3-hydroxymethyl-[1,2,4]oxadiazol-5-ylmethyl)-benzoic acid ethyl ester (80 mg, 0.41 mmol) in anhydrous CH2Cl2 (8 mL) under argon gas at room temperature. Add 1-(3-chloro-2,4-dihydroxy-phenyl)-ethanone (115 mg, 0.62 mmol) to the mixture, followed by diisopropyl azodicarboxylate (194 μL, 0.86 mmol). After 1.5 hours at room temperature, remove the polymer by filtration and concentrate the filtrate. Purify the residue by flash column chromatography using 30% ethyl acetate/hexane to give the title compound (60 mg, 34%). LC-MS (m/e): 429 (M−1).

Provenance & Evidence