Triphenylphosphine → (But-3-yn-2-yloxy) Benzene

Participants

Reaction Steps

Phenol 27 (422.9 mg, 4.49 mmol), But-3-yn-2-ol (300 mg, 4.28 mmol) were dissolved in anhydrous THF (10 mL) under N2 atmosphere, at 0° C. was added Ph3P (1.12 g, 4.26 mmol) portion wise, stirred it for 10 min, and then DEAD (894.6 mg, 5.14 mmol) added slowly. The resultant solution was heated up to 70° C. stirred for 20 h. To the reaction mixture water added and extracted with DCM and dried organic layer on MgSO4, filtered, concentrated. Purified by flash chromatography using ethylacetate/n-hexane, 5:95) provided compound 28 (450 mg, 69%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 1.67 (d, J=6.8 Hz, 3H), 2.47 (d, J=2 Hz, 1H), 4.88 (q, J=2 Hz, 1H), 6.97-7.03 (m, 3H), 7.28-7.32 (m, 2H).

Provenance & Evidence