Potassium Fluoride → P-[Tetrahydropyran-2-yloxy]phenylacetylene

Participants

Reaction Steps

KF (9.3 g, 160 mmol) was added to a stirred solution of 2 (22.6 g, 80 mmol) in MeOH (150 ml). The reaction mixture was stirred at room temperature for about 4 hours. After the reaction finished (GC shows no starting material remaining), the solvent was removed under reduced pressure on a rotary evaporator. The residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1) to give a pale yellow crystals of 3. Yield 15.7 g (97%); mp 65° C., δH (CDCl3, 300 MHz): 7.42 (d, J=8.7, 2H, Ar—H), 7.00 (d, J=8.7, 2H, Ar—H), 5.43 (t, J=3.2, 1H, OCHO), 3.87 (m, 1H, THP), 3.60 (m, 1H, THP), 2.99 (s, 1H, C═C—H), 1.96˜1.56 (m, 6H, THP).

Provenance & Evidence