Sodium hydride → HCID 66917857, compound

Participants

Reaction Steps

(E)-3-(1H-Indol-7-yl)-acrylic acid ethyl ester (K-45). To a 100 mL round bottom flask which contained a suspension of NaH (60% in mineral oil, 320 mg, 8 mmol) in THF (20 mL) was added triethylphosphonoacetate (1.5 g, 6.6 mmol) at 0° C. The resulting mixture was allowed to warm to room temperature and stir at for 2 h and then cooled to 0° C. To this solution, 1H-indole-7-carboxaldehyde (K-44, 450 mg, 3 mmol) was added at 0° C. The resulting reaction mixture was allowed to warm to room temperature and stir for 2 h, then heated and stirred at 78° C. for 14 h. The reaction mixture was cooled to 5° C. and was quenched with the addition of saturated aqueous NH4Cl (15 mL) followed by extraction of EtOAc (3×30 mL). The combined organic extracts were washed with brine (2×20 mL), dried (Na2SO4), filtered and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, EtOAc/hexane=1:20-1:8) to afford desired 3-(1H-indol-7-yl)-acrylic acid ethyl ester K-45 (450 mg, 68%) as a white solid. MS(ESI−) m/z(216.3, 100%). 1HNMR, 13CNMR.

Provenance & Evidence