Aluminium lithium hydride → HCID 58303839, compound

Participants

Reaction Steps

A solution of 17-2 (1.98 g, 4.874 mmol) in dry 1,4-dioxane (80 mL) was added dropwise to a slurry of LiAlH4 (1.85 g, 48.74 mmol) in dry 1,4-dioxane (40 mL) at reflux. The mixture was held at reflux for 1 h. The mixture was then cooled, quenched with 2 mL H2O, 2 mL NaOH (15%) solution, and 6 mL H2O. After stirring for 20 min, the mixture was filtered and the filtrate was concentrated. The resulting residue was purified by column chromatography on silica gel with hexanes/ethyl acetate (1:0 to 1:1) as eluent to afford 17-3 as a colorless oil in 56% yield (1.0 g). 1H NMR (300 MHz, CDCl3) δ (ppm) 7.97 (br, 1H), 7.47-7.50 (m, 2H), 7.34-7.43 (m, 3H), 6.96-6.98 (m, 3H), 5.27 (d, J=1.1 Hz, 2H), 3.74 (dt, J=6.3, 6.0 Hz, 2H), 2.96 (t, J=6.3 Hz, 2H), 1.47 (t, J=6.3 Hz, 1H). APCI [M+1]: 286.1

Provenance & Evidence