3,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone → 1,2,3,4-Tetrahydro-7-(2-quinolinylmethoxy)-1-naphthalenol

Participants

Reaction Steps

To a solution of 0.62 g (16.33 mmol) lithium aluminum hydride in 80 mL tetrahydrofuran under nitrogen at 0° C. is added dropwise with stirring a solution of 5.0 g (16.48 mmol) of 3,4-dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone over 1 minute. The ice bath is removed and after 1 hour the reaction is worked up according to Micovic and Mihailovic1. The crude product is recrystallized from ethylacetate/hexane and affords 3.1 g (62%) of white crystals, m.p. 113°-115° C.

Provenance & Evidence