Propargyl alcohol → HCID 18446528, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(2-bromo-thiophen-3-yl)-propionitrile 81 (0.5 g, 2.31 mmol), CuI (0.04 g, 0.23 mmol), PdCl2(PPh3)2 (0.08 g, 0.12 mmol) in NEt3 (6 mL) at room temperature was added propargyl alcohol (0.28 mL, 4.62 mmole) and the reaction mixture was stirred at 50° C. for 9 h. The mixture was concentrated in vacuo and purified by silica gel column chromatography (eluent: 50% EtOAc in hexane). The major fractions were combined and concentrated to give 82 (0.27 g) as a yellow syrup. 1H NMR (400 MHz, d6-DMSO) δ: 7.54 (d, J=5.0 Hz, 1H), 7.10 (d, J=5.0 Hz, 1H), 5.37 (t, J=6.0 Hz, 1H), 4.34 (d, J=6.0 Hz, 2H), 2.93 (t, J=7.0 Hz, 2H), 2.84 (t, J=7.0 Hz, 2H). MS (EI) m/z (M−OH+) 174.

Provenance & Evidence