Sodium Carbonate → 3-Propyl-benzofuran

Participants

Reaction Steps

To a solution of 1-but-2-enyloxy-iodobenzene (4.00 g, 13.8 mmol) in DMF (46 mL) was added n-Bu4NCl (5.36 g. 19.3 mmol), Pd(OAc)2 (0.168 g, 0.690 mmol), Na2CO3 (2.99 g, 28.2 mmol) and NaOAc (1.13 g, 13.8 mmol). The mixture was heated to reflux under nitrogen atmosphere overnight. The mixture was diluted with EtOAc and washed with water. The aqueous layer was extracted with EtOAc (3×). The combined organics were washed with brine and dried over Na2SO4. Purification by column chromatography (silica gel, hexanes) gave the title compound (1.79 g, 81%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.75 (s, 1H), 7.63-7.60 (m, 1H), 7.54 (d, J=7.5 Hz, 1H), 7.33-7.22 (m, 2H), 2.64-2.59 (m, 2H), 1.72-1.64 (m, 2H), 0.96 (t, J=7.2 Hz, 3H); ESI MS m/z 161 (M+H)+.

Provenance & Evidence