HCID 18717979, compound → HCID 22620126, compound

Participants

Reaction Steps

To a solution of 0.20 g of 3-[5-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol4-yl]-propionic acid methyl ester in 10 mL of toluene cooled to −75° C. under nitrogen was added 0.5 mL of 1.5 M diisobutylaluminum hydride. After 1 h at −75° C., the reaction was quenched with 0.2 mL of methanol, allowed to warm to room temperature over 30 min and partitioned between 1N sodium carbonate and ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The crude 3-[5-chloro-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-propionaldehyde (0.2 g) was essentially homogeneous by TLC, eluting with ethyl acetate.

Provenance & Evidence