Water → 5-Cyano-5-(diethoxy-phosphoryl)-4-(tetrahydro-pyran-4-yl)-pentanoic acid

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Reaction Steps

In a flask, [1-cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester (7.18 g, 21.6 mmol), dichloromethane (245 mL), acetic acid (70 mL), tetrabutylammonium bromide (490 mg), and water (210 mL) were combined and stirred at room temperature. KMnO4 (15.35 g, 97.2 mmol) was then added portionwise over the next 3 hours, and the reaction mixture was stirred overnight at room temperature. Solid NaHSO3 was added carefully until the reaction mixture became clear. The reaction mixture layers were separated, and the solvent was removed in vacuo to yield the title compound as a residue.

Provenance & Evidence