Aluminium lithium hydride → HCID 86662314, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 2-(6-chloropyridin-3-yloxy)-2-methylpropanoate (6.093 g, 25.0 mmol) in dry tetrahydrofuran (80 mL) is cooled to −20° C. (acetonitrile/dry ice bath) under nitrogen atmosphere. A solution of lithium aluminum hydride (1.0 M in THF, 35 ml) was added via drop-wise addition over 10 minutes. The mixture was stirred at −20° C. for 1 hour. The reaction was carefully quenched via addition of water (0.73 ml). The mixture was stirred for 10 minutes and then an aqueous solution of 5% sodium hydroxide (1.34 ml) was added with stirring for 10 minutes. Finally water (1.34 ml) was added and the mixture was stirred for 10 additional minutes. Magnesium sulfate was added and the material was filtered through a plug of celite, rinsing well with tetrahydrofuran. (Note that subsequent stirring of the aluminum salts in dichloromethane (50 ml) and filtering through celite provides additional product). The filtrates were stripped on the rotary evaporator, providing the desired product as a semi-viscous brown oil (4.843 g). (M+H)+=202 m/e.

Provenance & Evidence