Sodium Hydroxide → HCID 22600030, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-ethoxy-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetamide (35) (674 mg, 2.33 mmole) in 20 mL ether was treated with 400 mg of lithium aluminium hydride and heated at reflux for 3.5 hours. The reaction mixture was cooled to 0° C., treated successively with 0.4 mL water, 0.4 mL 15% aqueous sodium hydroxide solution, 1.2 mL water and stirred at room temperature until a white precipitate formed. MgSO4 was added and the mixture was filtered and concentrated in vacuo to give a pale brown oil. The product was purified by flash chromatography (SiO2, 10% ethyl acetate/hexanes), to yield 484 mg (75%) of (2-ethoxy-ethyl)-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-amine (37), as a pale yellow oil.

Provenance & Evidence