Triethylamine → (E)-5-(2-cyclohexylvinyl)furan-2-carbaldehyde

Participants

Reaction Steps

A mixture of 5-bromofuran-2-carbaldehyde (1.03 g, 5.89 mmol), vinylcyclohexane (0.86 g, 7.80 mmol), P(o-Tol)3 (0.089 g, 0.29 mmol), Pd(OAc)2 (0.070 g, 0.31 mmol) and Et3N (2.0 mL) in anhydrous DMF (3.0 mL) was degassed by bubbling Ar then alternating vacuum/Ar three times. The reaction mixture was heated under inert atmosphere at +90° C. for 20 hrs and cooled to room temperature. Aqueous NH4Cl was added to the reaction mixture and the mixture was extracted twice with hexanes and EtOAc. Combined organic layers were washed with brine, concentrated under reduced pressure. Purification by flash chromatography (3%-8% EtOAc—hexanes gradient) gave (E)-5-(2-cyclohexylvinyl)furan-2-carbaldehyde as a yellow oil. Yield (0.40 g, 33%); 1H NMR (400 MHz, CDCl3) δ 9.53 (s, 1H), 7.19 (d, J=3.8 Hz, 1H), 6.55 (dd, J=7.0, 16.1 Hz, 1H), 6.34 (d, J=3.5 Hz, 1H), 6.19-6.26 (m, 1H), 2.10-2.19 (m, 1H), 1.52-1.92 (m, 6H), 1.10-1.42 (m, 4H).

Provenance & Evidence