Hydrochloric Acid → Diethyl 2-(4-(4-chlorophenyl)-tetrahydro-2H-pyran-4-carbonyl)malonate

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To a solution of 4-(4-chlorophenyl)tetrahydro-2H-pyran-4-carboxylic acid (0.500 g, 2.08 mmol) in IPAc (2.5 mL) was added DMF (0.050 mL). Oxalyl chloride (0.277 g, 0.19 mL, 2.18 mmol) was then added at ambient temperature over a period of 20 minutes. The resulting solution was stirred at room temperature for a period of 2 hours. In a separate flask, a solution of diethyl malonate (0.420 g, 0.40 mL, 2.60 mmol) in IPAc (3.5 mL) was treated with MgCl2 (0.247 g, 2.60 mmol). The resulting slurry was aged at room temperature for 30 minutes and subsequently treated with TEA (0.704 g, 0.97 mL, 2.60 mmol). After a further 2 hours at ambient temperature, the malonate slurry was cooled to 5° C. and treated with the acyl chloride solution. The resulting mixture was aged at room temperature for 2 hours then treated with a 5N HCl solution (2.5 mL). The organic layer was separated, and the aqueous layer was extracted 3 times with IPAc (2.5 mL). The organic phases were combined, dried (MgSO4), and concentrated under reduced pressure to afford the title compound as an orange oil. MS m/e=383.2 (M+H)+.

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