Dimethylformamide → Benzofuran-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of triflate 20-3 (0.798 g, 3.0 mmol), Pd(OAc)2 (13.5 mg, 0.060 mmol), and diphenylphosphinopropane (24 mg, 0.060 mmol) in DMF (15 mL) was heated to 70° C. with a gentle flow of CO (g) passing through it. Triethylamine (1.66 mL, 12 mmol) was added followed by trioctylsilane (2.70 mL, 6.0 mmol). The solution was maintained at 70° C. for 2 h, and cooled to room temperature. The solution was diluted with water (10 mL). The mixture was extracted with Et2O (2×30 mL). The combined organic extracts were washed with brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (5% acetone/hexanes) to give the desired aldehyde 20-4.

Provenance & Evidence