Diisobutylaluminum hydride → HCID 68162254, compound

Participants

Reaction Steps

(E)-3-Imidazo[1,2-a]pyridin-7-yl-acrylic acid ethyl ester (prepared according to Procedure H1 to H4 using triethylphosphono acetate, 519 mg, 2.4 mmol) was dissolved in a mixture of toluene/dichloromethane (1:1, 12 ml) and cooled on a dry ice/acetone bath. Diisobutylaluminium hydride (1 M in toluene, 3 ml) was added dropwise. After 45 minutes the reaction was transferred to a salt/ice bath and further portions of DIBAL were added until the reaction was complete. The reaction was quenched by the cautious addition of methanol and was allowed to warm to room temperature. The reaction was concentrated in vacuo and 2N sodium hydroxide solution was added. This was extracted twice with dichloromethane and the combined liquors were dried and concentrated to furnish the desired monomer (327 mg) as a yellow solid MS: [M+H]+=175

Provenance & Evidence