Aluminium lithium hydride → HCID 86722315, compound

Participants

Reaction Steps

To a cooled (−78° C.) solution of methyl 4-(3-(2-hydroxyethyl)-3-methylureido)benzoate (2.02 g, 8.00 mmol) in THF (80 mL) was added a solution of lithium aluminium hydride (2.0 M solution in THF, 6.0 mL, 12.0 mmol). After 20 minutes the coolant was removed and the reaction mixture stirred at RT for 18 h. The reaction mixture was quenched with water (0.46 mL), 2 M aqueous sodium hydroxide (0.46 mL) and water (3×0.46 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture stirred for 1 hour and then filtered. The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0 to 100% ethyl acetate/iso-hexane to afford the title compound (1.09 g, 60%).

Provenance & Evidence