Sodium Hydroxide → HCID 22596837, compound

Participants

Reaction Conditions

Reaction Steps

A solution of hexanoic acid (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amide (740 mg, 2.46 mmole) in 20 mL diethyl ether (ether) was treated with 400 mg of lithium aluminium hydride (LAH) and the mixture was heated to reflux for 90 minutes. After cooling to 0° C., 0.4 mL of water, 0.4 mL of 15% aqueous sodium hydroxide solution and 1.2 mL of water were successively added and the reaction mixture was stirred at room temperature for 30 minutes. MgSO4 was added and the mixture was filtered and concentrated in vacuo to provide a pale yellow oil. The product was purified by flash chromatography SiO2, 5% ethyl acetate/hexanes) to yield 635 mg (81%) of hexyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (17) as a colorless oil.

Provenance & Evidence