2-Thiophenecarboxaldehyde → 11-(2-Thienyl)-10-undecenoic acid

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Reaction Steps

This compound was synthesized from 2-thiophenecarboxaldehyde (2.24 g, 20 mmol) and 9-carboxynonyltriphenylphosphonium bromide (10.27 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Crystallization (hexanes-ethyl acetate) afforded the product (2.45 g, 46%) as white crystals (mp 61-62° C.); IR: 3450-2500, 1715 cm-1 ; 1H-NMR: 1.31 (m, 8 H), 1.45 (m, 2 H), 1.65 (m, 2 H), 2.34 (t, 2 H), 2.38 (t, 2 H), 5.55 (m, 1 H), 6.50 (d, 1 H), 6.95 (m, 2 H), 7.23 (d, 2 H), 10.05 (bs, 1 H). Anal. Calcd. for C15H22O2S: C, 67.63, H, 8.32%; Found: C, 67.60, H, 8.34%. Z:E=19:81.

Provenance & Evidence