Aluminium lithium hydride → HCID 22600035, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phenylacetic acid (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amide (7) (790 mg, 2.46 mmole) in 20 mL diethyl ether (ether) was treated with 400 mg of lithium aluminium hydride (LAH) and heated at reflux for 90 minutes. After cooling the reaction flask to 0° C., the reaction mixture was quenched by successive addition of 0.4 mL water, 0.4 mL of 15% aqueous sodium hydroxide solution and 1.2 mL water. The mixture was stirred at room temperature for 30 minutes and MgSO4 was added. After filtration, the mixture was concentrated in vacuo, to provide a pale yellow oil. The product was purified by flash chromatography (SiO2, 5% ethyl acetate/hexanes), yielding 619 mg (82%) of phenethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (9) as a pale yellow oil.

Provenance & Evidence