HCID 67418235, compound → HCID 67379178, compound

Participants

Reaction Steps

A suspension of 10% palladium on carbon (146 mg, 0.137 mmol) in a solution of methyl 2-(acetyloxy)-5-[(1Z)-3-hydroxyprop-1-en-1-yl]-3-methylbenzoate (362 mg, 1.370 mmol) in EtOAc (17.2 mL) was shaken in a Parr shaker under H2 at 40 psi overnight. The reaction mixture was filtered through a plug of Celite and washed through with EtOAc. The filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 60% EtOAc in hexanes over 1125 mL) to afford methyl 2-(acetyloxy)-5-(3-hydroxypropyl)-3-methylbenzoate, as a colorless oil. LCMS calc.=289.1; found=288.9 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 7.65 (d, J=2.2 Hz, 1 H); 7.25 (d, J=2.2 Hz, 1 H); 3.84 (s, 3 H); 3.64 (t, J=6.4 Hz, 2 H); 2.67 (t, J=7.8 Hz, 2 H); 2.35 (s, 3 H); 2.18 (s, 3 H); 1.89-1.82 (m, 2 H).

Provenance & Evidence