Propargyl alcohol → (4,6-Dichlorobenzofuran-2-yl)methanol

Participants

Reaction Steps

Propargyl alcohol (0.12 ml; 1.96 mmol) was added drop wise to a refluxing mixture of the product of Step D (0.55 g; 1.96 mmol) and Cu2O (0.2 g; 1.4 mmol) in anhydrous pyridine (4 ml) under N2. After refluxing for 1 h, the solvent was removed under reduced pressure and the residue was treated with EtOAc (15 ml). The insoluble material was filtered off and the filtrate was washed with 10% citric acid, H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.24 g; 56%) as colourless solid. 1H-NMR (CDCl3) 1.91 (tr, 1H, J=6.3 Hz); 4.75 (d, 1H, J=6.3 Hz); 6.72 (s, 1H); 7.23 (s, 1H); 7.37 (s, 1H).

Provenance & Evidence