2-Thiophenecarboxaldehyde → 9-(2-Thienyl)-8-nonenoic acid

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Reaction Steps

This compound was synthesized from 7-carboxyheptyl-triphenylphosphonium bromide (9.71 g, 20 mmol) and 2-thiophenecarboxaldehyde (2.24 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization afforded the product (2.79 g, 59%) as white crystals (mp 45-46° C.). IR: 3400-2500, 1720, 710 cm-1 ; 1H-NMR: 1.45 (m, 8H), 2.35 (m, 4H), 5.55 (m, 1H), 6.50 (d, 1H), 7.00 (m, 3H), 11.00 (bs, 1H). Anal. Calcd. for C13H18SO2 : C, 65.51, H, 7.61%; Found: C, 65.58, H, 7.63%. Z:E=75:25.

Provenance & Evidence