Isonicotinic Acid → HCID 8027287, compound

Participants

Reaction Steps

A mixture of isonicotinic acid (114.4 g, 0.93 mol), PPh3 (333.2 g, 1.27 mol) and alcohol 3c (110 g, 0.85 mol), in THF (1.1 L) is treated with DIAD (249.5 mL, 1.3 mol) dropwise at 0° C. After stirring for 30 min, the cooling bath is removed and the mixture is stirred at RT for 2 h. The mixture is filtered and then concentrated. The residue is triturated with Et2O and the ether layers are extracted with 30% HCl. The combined aqueous phases are washed with Et2O (2×) and EtOAc (2×) and then neutralized with Na2HPO4 to about pH 6. The neutralized aqueous phase is extracted with Et2O (5×) and then DCM (3×). The combined ether layers are dried (MgSO4) and concentrated in vacuo. The DCM layers are combined and dried (MgSO4), concentrated in vacuo and combined with the product resulting from the ether extractions to afford ester 3d.

Provenance & Evidence