Propargyl alcohol → HCID 67373277, compound

Participants

Reaction Steps

Triethylamine (0.943 mL, 6.76 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.092 g, 0.132 mmol) were added to a mixture of methyl 2-(acetyloxy)-5-iodo-3-methylbenzoate (1.0 g, 2.99 mmol) and propargyl alcohol (0.161 mL, 2.69 mmol) in THF (20 mL) at room temperature, and then copper (I) iodide (0.053 g, 0.278 mmol) was added. The resulting mixture was stirred at room temperature for 18 h. The reaction was quenched with water (20 mL) and extracted with EtOAc (3×30 mL). The combined organic extracts were washed with water (50 mL), brine (40 mL), dried (MgSO4), and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 0-20% EtOAc in hexanes over 30 min) to afford methyl 2-(acetyloxy)-5-(3-hydroxyprop-1-yn-1-yl)-3-methylbenzoate, as a yellow solid. 1H NMR (500 MHz, CHCl3): δ 7.97 (s, 1 H); 7.53 (s, 1 H); 4.91 (s, 2 H); 3.88 (s, 3 H); 2.22 (s, 3 H); 2.16 (s, 3 H).

Provenance & Evidence