1-Tridecyne → 3-(1-Tridecynyl)furan-2-carboxaldehyde

Participants

Reaction Steps

Reaction of 3-bromofuran-2-carboxaldehyde (3.86 g, 21.5 mmole, from Example 5) with 1-tridecyne (6.7 g) as described in Example 1 afforded 2.28 g (39% of the title compound after chromatography with dichloromethane on silica. Recrystallisation from petroleum ether [bp 40°-60° C.] afforded material of mp 56°-57° C., νmax 3170, 3120, 2230, 1660, 1420, 1355, 1280 cm-1 ; δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.11-1.67 (18H, m, alkylene chain), 2.40 (2H, t, J 6.3 Hz, CH2C≡C), 6.47 (1H, d, J ca 2 Hz, C-4H), 7.51 (1H, d, J ca 2 Hz, C-5H), 9.71 (1H, s CHO).

Provenance & Evidence