Ammonium formate → HCID 21463007, compound

Participants

Reaction Steps

A solution of 1-(pyridin-4-yl)-2-(furan-2-yl)ethene (15.0 g, 87.7 mmol) [Example 18, Step 1] in methanol (300 ml) was treated with ammonium formate (27.6 g, 438.5 mmol) and 10% palladium on charcoal catalyst (1.5 g, 10% (w/w)). The mixture was stirred at reflux for 3 hours. The catalyst was removed by filtration and the solvent was evaporated in vacuo. The residue was partitioned between dichloromethane and water. The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was chromatographed with 1:1 hexane/ethyl acetate as eluant to afford the title compound as a colourless oil (3.0 g, 19%); δH (DMSO-d6) 1.35-1.50 (1H, m, tetrahydrofuranyl H), 1.70-2.00 (5H, m, CH2 and 3×tetrahydrofuranyl H), 2.54-2.76 (2H, m, CH2), 3.54-3.82 (3H, m, tetrahydrofuranyl H), 7.22 (2H, d, J 7.1 Hz, ArH), and 8.46 (2H, d J 7.0 Hz, ArH); m/z (CI+, NH3) 178 (M+1)+.

Provenance & Evidence