Hydrochloric Acid → 2-(4-Hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

Participants

Reaction Conditions

Reaction Steps

A solution consisting of 58 (1.5 g, 4.9 mmol) in DMF (25 mL) was treated with CulBr (1.0 g, 6.5 mmol) and NaOMe (6 mL, 4.4 N in MeOH, 27 mmol) and heated to 160° C. for approximately 1 hour. The reaction mixture was allowed to cool and then worked up by adding 2 N HCl and EtOAc. The EtOAc layer was washed with NaHCO3 aq, brine and dried over MgSO4. The solution was concentrated and chromatographed on silica gel (1:4 EtOAc/hexanes to 3:7 EtOAc/hexanes) to yield 0.47 g of pdt: Mp=167–168° C., 1H NMR (DMSO-d6) δ 9.84 (br s, 1 H), 9.18 (br s, 1 H), 7.67 (d, 2 H, J=8.6 Hz), 6.99 (s, 1 H), 6.86 (d, 2 H, J=8.7 Hz), 6.46 (d, 1 H, J=2.1 Hz), 6.34 (d, 1 H, J=2.1 Hz), 3,89 (s, 3 H); MS 257 (M+H)+.

Provenance & Evidence