1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenoxy}ethanol

Participants

Reaction Steps

To a solution of (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.10 g, 0.21 mmol) in methanol (0.60 mL), DBU (0.079 mL, 0.53 mmol) was added and 2-(2-hydroxyethoxybenzaldehyde (0.039 g, 0.23 mmol) was further added, followed by stirring at room temperature for 2.0 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5). The obtained compound was added with 2.0 mol/L hydrogen chloride-ethyl acetate solution (2.0 mL) and washed, then the precipitated solid was collected by filtration. The obtained solid was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution to separate the mixture into organic layer and aqueous layer. The organic layer was concentrated under reduced pressure and the residue was dried under reduced pressure to obtain Compound 134 (0.024 g, 9%).

Provenance & Evidence