3-Dodecylthiophene-2-carbaldehyde → (E)-1,2-bis(3-dodecylthienyl)ethylene

Participants

Reaction Steps

To a suspension of low-valent Ti prepared from TiCl4 (0.94 mL, 8.56 mmol) and Zn (1.12 g, 17.11 mmol) in 42 mL of dry THF under N2 at 0° C. was added a dry solution of 11 (2 g, 7.13 mmol) in 14 mL of dry THF. After 2 h of refluxing, the mixture was cooled to room temperature, filtered to remove excess Zn, evaporated, poured into water and extracted with CH2Cl2. The organic phase was washed with water and dried over MgSO4. After solvent removal, the crude solid was purified by column chromatography (silica gel, hexane) to give a pale yellow solid compound 12 in 75% yield. 1H-NMR (CDCl3, 400 MHz) ppm 0.88 (t, 6H, J=6.8 Hz) ppm 1.31 (m, 36H) ppm 1.59 (td, 4H, J=7.4 Hz, J=14.7 Hz) ppm 2.65 (m, 4H) ppm 6.84 (d, 2H, J=5.2 Hz) ppm 6.99 (s, 2H) ppm 7.07 (d, 2H, J=5.2 Hz).

Provenance & Evidence