Propargyl alcohol → 1-Benzofuran-2-Ylmethanol

Participants

Reaction Conditions

Reaction Steps

2-Iodophenol (500 mg, 2.27 mmol), propargyl alcohol (265 μl, 4.54 mmol), Pd(OAc)2, (5.1 mg, 0.03 mmol), triphenylphosphine (12 mg, 0.046 mmol), n-butylamine (450 μL, 4.5 mmol) and CuI (8.6 mg, 0.045 mmol) were combined in 4.5 mL of THF and the mixture was heated at 40° C. under nitrogen for 36 h. The mixture was cooled to room temperature and the solvents were removed in vacuo and the residue purified by SiO2 column chromatography on 100 g of silica gel, eluting with 20% ethyl acetate in hexanes. 2-(Hydroxymethyl)benzofuran was obtained by concentration of the product containing fractions. [Kudu, N. G.; Pal, M.; Mahanty, J. S.; Dasgupta, F. K. JCS Chem. Com. 1992, 41]

Provenance & Evidence