Aluminium lithium hydride → HCID 71735771, compound

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Reaction Steps

Compound 1b (1.5 g, 6.1 mmol) was dissolved in anhydrous THF (50 mL). LiAlH4 (500 mg, 13 mmol) was added to the mixture under argon. The reaction mixture was heated to reflux for 4 hr. After cooling to room temperature, the reaction was carefully quenched with water (50 mL). The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by flash chromatography on silica gel to provide the product compound 1 (190 mg, 0.83 mmol, 14% yield) as a pale-yellow powder. HRMS (ESI, positive) m/z calcd. for C14H16NO2 [M+H]+: 230.1181, found: 230.1190; m/z calcd. for C14H15NO2Na [M+Na]+: 252.1001, found: 251.1061. 1H NMR (CDCl3, 400 MHz) δ 7.25 (t, J=8.6 Hz, 2H), 6.83-6.76 (m, 5H), 6.71 (d, J=7.2 Hz, 2H), 4.12 (t, J=5.0 Hz, 2H), 3.52 (t, J=5.0 Hz, 2H).

Provenance & Evidence