Methanol → Methyl 5-cyano-5-(2-fluorophenyl)-2-oxocyclohexanecarboxylate

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Reaction Steps

Dimethyl 4-cyano-4-(2-fluorophenyl)heptanedioate (D18, 35.86 g, 0.12 mol) was stirred under Ar in toluene (500 ml) as sodium hydride (80% in mineral oil, 3.5 g, 0.12 mol) was added. Methanol (10 ml) was added dropwise, and the mixture was then stirred at reflux for 16 h, partitioned between ethyl acetate and dilute HCl, and separated. The organic portion was washed with brine, dried (Na2SO4) and evaporated to an oil. This was dissolved in dichloromethane (500 ml), filtered, and evaporated to give the title compound (30.66 g, 95%) as a cream solid.

Provenance & Evidence