Sodium hydride → HCID 73990329, compound

Participants

Reaction Steps

Solid NaH (396 mg, 16.5 mmol) was added in small portions into a suspension of 4-(4′vinylstyryl)benzaldehyde (703 g, 3.0 mmol) and 4-tert-butylbenzyltriphenylphosphonium bromide (1.61 g, 3.3 mmol). The reaction mixture was stirred under nitrogen at room temperature for 24 hours. The reaction was quenched slowly with water, extracted with CHCl3, washed with brine, and the solvent was evaporated under reduced pressure to dryness. To the residue, 100 mL of dry toluene was added and evaporated to dryness. The light yellow solid was triturated with ethanol, filtered to give light yellow solid (which is the all-trans isomer by NMR). The filtrate was concentrated and purified with silica gel chromatography (10-20% CHCl3/hexanes) to give another portion of product (a mixture of cis and trans isomers). Yield: 1.1 g (>99%). 1H NMR (CDCl3) of the all-trans isomer: δ 7.51 (s, 4H), 7.49, 7.47 (d, J=8.46 Hz, 4H), 7.41, 7.39 (d, J=8.45 Hz, 4H), 7.13, 7.07 (d, J=16.28 Hz, 2H), 7.11 (s, 2H), 6.72 (dd, J1=10.85 Hz, J2=17.55 Hz, 1H), 5.78 (d, J=17.55 Hz, 1H), 5.26 (d, J=10.85 Hz, 1H), 1.34 (s, 9H). The compound is too insoluble for 13C NMR spectroscopy.

Provenance & Evidence