Aluminium lithium hydride → HCID 59004652, compound

Participants

Reaction Steps

To a dry argon purged flask fitted with a magnetic stirbar, condenser and dropping funnel is charged lithium aluminum hydride (80.9 mg, 2.131 mmol), anhydrous diethyl ether (10 mL) and stirring begun. A solution of compound 34 (360 mg, 1.421 mmol) in anhydrous diethyl ether (10 mL) is charged to the dropping funnel and added drop wise to the LiAlH4 suspension and mixture stirred at ambient temperature for 30 minutes. The reaction was quenched by the sequential addition of 100 ul H2O, 125 ul 3M sodium hydroxide and 300 ul H2O. After filtration to remove insolubles, the solution was concentrated and the residue purified twice via chromatography on silica gel (2M NH3 in methanol:CH2Cl2, 5:95 to 1:9) to afford pale yellow oil 36 (149 mg, 40.7%); 1H NMR (DMSO-d6) δ 7.45 (s, 1H), 7.37-7.33 (2×m, 2H), 7.10 (d, 1H, J=8.2 Hz), 6.35 (d, 1H, J=3.1 Hz), 4.15 (t, 2H, J=7.4 Hz), 3.76 (s, 2H), 2.93-2.87 (m, 1H), 2.15 (s, 3H), 2.12-2.03 (m, 1H), 2.00-1.93 (m, 2H), 1.88-1.79 (m, 1H), 1.68-1.52 (m, 3H), 1.44-1.35 (m, 1H); ESI-MS (m/z, %): 258 (M+1, 100%).

Provenance & Evidence