Aluminium lithium hydride → HCID 24887414, compound

Participants

Reaction Steps

A 100 mL round bottom flask containing nitrile 27 (700 mg, 1.88 mmol) in THF (25 mL) was charged with lithium aluminum hydride (285 mg, 7.52 mmol). After stirring at room temperature for 45 minutes, the reaction mixture was poured into an 1.0 L Erlenmeyer flask and quenched with 200 mL ethyl acetate, 10 mL water, sodium sulfate, and an excess of 2:1 Na2SO4 10H2O:celite. The mixture was filtered, then concentrated under reduced pressure, and then dissolved in a minimum volume of CH2Cl2, then loaded onto a 40 g Isco RediSep normal phase silica cartridge, and purified on an Isco OptiX10 CombiFlash instrument using a gradient that started at 100% methylene chloride and ended at 90% methylene chloride, 9% methanol, 1% concentrated ammonium hydroxide. Fractions containing desired product were pooled and concentrated under reduced pressure. Yield of 28: 196 mg (28%). 1H NMR (500 MHz, CDCl3) δ 1.38 (s, 6H), 2.89 (s, 2H), 5.14 (bs, 2H), 6.54 (d, J=5.5 Hz, 1H), 6.97 (dd, J=7.5, 2.0 Hz, 1H), 7.14 (m, 2H), 7.65 (m, 3H), 8.13 (d, J=5.5 Hz, 1H), 9.46 (dd, J=7.5, 0.5 Hz, 1H). MS (ESI+) 377.2.

Provenance & Evidence