Triethylamine → Phosphonium, [[5-(4-fluorophenyl)-2-oxazolyl]methyl]triphenyl-, chloride (1:1)

Participants

Reaction Steps

[5-(4-fluorophenyl)-1,3-oxazol-2-yl]methanol (0.46 g, 2.4 mmol) was dissolved in DCM (5 ml), then Et3N (0.3 ml, 2.4 mmol) and SOCl2 (0.35 ml,4.7 mmol) were added. The reaction mixture was stirred for 1 hour at room temperature under nitrogen. The mixture was diluted with DCM (20 ml) and a saturated solution of Na2CO3 (20 ml) was added carefully. The organic layer was separated, washed with brine (20 ml), dried over MgSO4 and concentrated in vacuo to give a yellow oil. This oil (0.5 g, 2.38 mmol) was treated with an equimolar amount of triphenylphosphine as described for Intermediate A (Step 3) to give the title compound. δH (360 MHz, DMSO) 5.76 (2H, d, J 16.0), 7.29 (2H, t, J 7.0), 7.39-7.46 (2H, m), 7.61 (1H, s), 7.74-7.95 (15H, m).

Provenance & Evidence