3,4-dihydro-2H-pyran → HCID 90409410, compound

Participants

Reaction Steps

A solution of 5-bromo-2,3-difluorophenol (2.75 g, 13.16 mmol), 3,4-dihydro-2H-pyran (2.39 mL, 26.3 mmol) and PPTS (0.165 g, 0.658 mmol) in DCM (10 mL) was stirred for 1 h at rt. At this time, analytical HPLC showed that the reaction was complete. The reaction was concentrated in vacuo. The crude oily product was chromatographed [SiO2; continuous gradient of EtOAc/hexane (0% to 20% over 15 min)] to give the title compound (2.5 g, 8.5 mmol, 65% yield) as a clear oil. 1H NMR (CDCl3) δ: 7.17 (dt, J=6.4, 2.2 Hz, 1H), 6.99 (ddd, J=8.8, 6.2, 2.4 Hz, 1H), 5.45 (t, J=3.0 Hz, 1H), 3.88 (td, J=11.0, 3.0 Hz, 1H), 3.72-3.62 (m, 1H), 2.11-1.82 (m, 3H), 1.80-1.59 (m, 3H); 19F NMR (CDCl3) δ: −135.00, −158.84.

Provenance & Evidence