Triphenylphosphine → HCID 68545252, compound

Participants

Reaction Steps

Methyl 4-methoxysalicylate (7.91 g, 43.4 mmol), 2-(4-tert-butoxycarbonylpiperazin-1-yl)ethanol (10.0 g, 43.4 mmol), and triphenylphosphine (PPh3) (11.3 g, 43.4 mmol) in THF (190 ml) were cooled to 0° C. under N2. DIAD (8.54 ml, 43.4 mmol) was added dropwise, and the reaction allowed to warm to room temperature. After stirring for 18 h, the THF was removed in vacuo, the residue taken up in dichloromethane, and washed with water, dried, and the solvent removed in vacuo to give a yellow oil. After the oil was dissolved in diethyl ether and the solution allowed to stand for 18 h, the triphenylphosphine oxide was filtered, the solvent removed in vacuo, and the crude product purified on silica gel using preparative HPLC and a gradient of hexane and EtOAc to give 11.0 g (64.3%) of a pale yellow oil.

Provenance & Evidence