Hydrochloric Acid → 3-Oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid

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Reaction Steps

Sodium hydroxide (1M, 74 mL, 0.074 mol) was added to a stirred solution of compound 3a (3.73 g, 0.018 mol) in methanol (105 mL) at room temperature. After 4 h, the reaction mixture was neutralized with 3M HCl, evaporated and co-evaporated with toluene several times. Pyridine (75 mL) and Ac2O (53 mL) were added and the reaction mixture was allowed to shake overnight at room temperature. The mixture was then co-evaporated with toluene and purified by flash column chromatography (ethyl acetate+1% acetic acid) which gave the title compound (2.51 g, 88%) as a yellow oil.

Provenance & Evidence