HCID 67373277, compound → HCID 67418235, compound

Participants

Reaction Steps

A suspension of methyl 2-(acetyloxy)-5-(3-hydroxyprop-1-yn-1-yl)-3-methylbenzoate (0.417 g, 1.590 mmol) and palladium on carbon (170 mg, 1.597 mmol) in EtOAc (20 mL) was stirred at room temperature under a balloon atmosphere of H2 for 3 days. The reaction mixture was filtered through a plug of Celite and washed through with EtOAc (3×30 mL). The filtrate was concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 0-20% EtOAc in hexanes over 40 min) to afford methyl 2-(acetyloxy)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-3-methylbenzoate, as a pale yellow oil. 1H NMR (500 MHz, CHCl3): δ 7.69 (s, 1 H); 7.29 (s, 1 H); 6.53 (d, J=12 Hz, 1 H); 5.94 (m, 1 H); 4.44 (d, J=6.4 Hz, 2 H); 3.88 (s, 3 H); 2.40 (s, 3 H); 2.25 (s, 3 H).

Provenance & Evidence