Sodium Chloride → 6-Methoxy-2-methylbenzofuran

Participants

Reaction Steps

A pressure tube was charged with a stir bar 2-Iodo-5-methoxyphenol (500 mg, 2.0 mmol) (prepared according to Heterocycles 45, (6), 1997, 1137), Cl2Pd(PPh3)2 (70 mg, 0.1 mmol), Cul (19 mg, 0.1 mmol), 1,1,3,3-Tetramethylguanidine (2.5 ml, 20.0 mmol) and DMF (10 ml), then cooled to −78° while propyne gas was condensed. The tube was sealed and allowed to warm to room temperature. After 18 hours, the contents of the tube were poured into sat NaCl solution and extracted with EtOAc (2×). The combined organic layers were washed with brine (3×), dried (MgSO4) and concentrated under reduced pressure. The residue was flash chromatographed on silica gel eluting 3:1 (hexanes/ethyl acetate) to give 239 mg (74%) of an amber liquid. 1H NMR (DMSO-d6) δ 7.31 (1H, d, J=8.3 Hz), 6.95 (1H, d, J=2.2 Hz), 6.80 (1H, dd, J=2.2, 8.3 Hz), 6.27 (1H, s), 3.85 (3H, s), 2.40 (3H, s). Anal. Calcd for C10H10O2.0.05 hexanes: C, 74.30; H, 6.48. Found: C, 74.63; H, 6.48.

Provenance & Evidence