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0 °C

A dry round bottom flask was charged with trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (2.00 g, 10.74 mmol) and the reaction vessel was placed under an atmosphere of argon (3× vacuum/argon cycle). Dichloromethane (11 mL) was added followed by DMF (0.01 mL, 0.129 mmol). The reaction was cooled to 0° C. in an ice bath, then oxalyl chloride (1.00 mL, 11.42 mmoles) was added drop-wise. The ice bath was removed after 1 hour and the reaction was stirred at ambient temperature for 14 hours as gradual gas evolution occurred. [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (236.0 mg, 0.322 mmol) was then added to the reaction flask followed by tetrahydrofuran (11 mL) then a solution of diethylzinc in tetrahydrofuran (1.0 M, 12.9 mL, 12.9 mmol). The reaction was stirred at ambient temperature for two hours and was then poured into cold saturated aqueous ammonium chloride (100 mL). The resulting biphasic solution was diluted with diethyl ether (100 mL). The organic phase was separated and dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes) to afford methyl trans-4-propanoylcyclohexanecarboxylate as a clear oil. 1H NMR (500 MHz, CDCl3) δ 3.67 (s, 3H), 2.47 (q, J=7.3 Hz, 2H), 2.40-2.21 (m, 2H), 2.12-2.00 (m, 2H), 1.94 (d, J=13.9 Hz, 2H), 1.53-1.20 (m, 4H), 1.03 (t, J=7.3 Hz, 3H).

1. customThe ice bath was removed after 1 hour
2. stirringThe reaction was stirred at ambient temperature for two hours
3. customThe organic phase was separated
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes)