HCID 18446528, compound → HCID 18446529, compound

Participants

Reaction Steps

To a stirred solution of 3-[2-(3-hydroxy-prop-1-ynyl)-thiophen-3-yl]-propionitrile 82 (0.27 g, 1.39 mmol) was dissolved in MeOH (5 mL). To this solution was added Pd/C [10% w/w] (0.15 g, 0.14 mmol). The mixture was then stirred under an atmosphere of hydrogen at room temperature for 4 h then filtered through a Celite pad and concentrated in vacuo. Purification by silica gel column chromatography (eluent: 50% EtOAc in hexane) afforded 83 (0.18 g) as a colorless syrup. 1H NMR (400 MHz, d6-DMSO) δ: 7.27 (d, J=5.0 Hz, 1H), 6.94 (d, J=5.0 Hz, 1H), 4.51 (t, J=5.0 Hz 1H), 3.42 (dd, J=6.0 Hz and 11.5 Hz, 2H), 2.82–2.71 (m, 6H), 1.70 (m, 2H). MS (EI) m/z (M+H+) 196, (M−OH+) 178.

Provenance & Evidence