Diisobutylaluminum hydride → 4-(Quinolin-3-yl)-but-3-en-2-ol

Participants

Reaction Steps

A solution of 22-1 (1.2 g, 6.1 mmol) in anhydrous THF (50 mL) was cooled to −78°, then treated dropwise with i-Bu2AlH (12.75 mL, 12.2 mmol). The resulting solution was stirred at −78° for 20 min, then quenched with ethyl acetate (20 mL), warmed to room temperature, treated with 1 M potassium sodium tartrate (25 mL) and stirred for 4 h. The mixture was extracted with ethyl acetate (2×150 mL) dried, filtered and evaporated to afford 22-2 as a yellow oil.

Provenance & Evidence