1,4-Dioxane → HCID 57016694, compound

Participants

Reaction Steps

A solution of 1-methyl-4-(p-fluorophenyl)-3-pyridiniumolate 27 (2.45 g, 12.04 mmol) and (+)-(R)-p-tolyl vinyl sulphoxide (2.00 g, 12.04 mmol).in dioxane (25 mL) was allowed to reflux for 20 hours. The resulting reaction mixture was concentrated under reduced pressure, purified by silica gel flash chromatography, and recrystallized from EtOAc to give the compound 30 as a white solid; [α]25D −77° (c 1.25, CHCl3); Rf0.2 (EtOAc/hexane, 7/3); mp 186° C. (EtOAc); 1H NMR (CDCl3) δ1.64 (dd, H7α, J=8.7 and 14.7 Hz), 2.14 (ddd, H7β, J=3.6, 7.8 and 14.7 Hz), 2.42 (s, 3H), 2.62 (s, 3H), 3.33 (dd, H6, J=3.6 and 8.7 Hz), 3.73 (d, H1, J=7.5 Hz), 4.51 (d, H5, J=5.4 Hz), 7.01 (d, H4, J=5.4 Hz), 7.041 (t, 2H, J=8.7 Hz), 7.30-7.40 (m, 4H), 7.66 (d, 2H, J=8.1 Hz).

Provenance & Evidence