Ethanol → Methyl 3-cyano-4-isopropoxybenzoate

Participants

Reaction Conditions

Reaction Steps

In a high-pressure reactor, compound 3 (1.76 g, 7.2 mmol) was dissolved in EtOH (40 mL). Triethylamine (5.0 mL 35.8 mmol) was added, followed by [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (188 mg, 0.36 mmol). The reaction vessel was pressurized with carbon monoxide (100 psi), evacuated and repressurized with carbon monoxide (100 psi). The vessel was evacuated and then pressurized again with carbon monoxide (350 psi). The reaction was heated to 90° C. and stirred for 16 h. It was cooled to room temperature, depressurized and filtered through celite. The solvents were evaporated, and the remaining residue was partitioned between dichloromethane (150 mL) and 1 M aqueous KHSO4 (75 mL). The layers were separated and the organic phase was washed with additional 1 M aqueous KHSO4 (1×75 mL). The organic phase was dried (Na2SO4) and concentrated to an oil which was purified using silica gel (EtOAc/Hexanes), providing compound 4 (648 mg, 2.70 mmol, 38% yield) as a white solid, characterized using 1H NMR.

Provenance & Evidence