Tetrahydrofuran → 2-{[(1H-Inden-7-yl)oxy]methyl}-4-(propan-2-yl)morpholine

Participants

Reaction Steps

In 50 ml. of anhydrous tetrahydrofuran was suspended 0.5 g. of lithium aluminum hydride and after adding slowly to the suspension a solution of 2.0 g. of 2-(7-indenyloxymethyl)-4-isopropylmorpholin-5-one in 10 ml. of anhydrous tetrahydrofuran with stirring, the mixture was stirred for 10 hours at 40°-50° C. Then, to the reaction mixture thus formed were added 0.5 ml. of water, 0.5 ml. of an aqueous 15% sodium hydroxide solution, and then 1.5 ml. of water successively to decompose excess lithium aluminum hydride. After stirring the mixture for 30 minutes, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue formed was dissolved in a small amount of ethyl acetate and the solution was subjected to a silica gel column chromatography (column diameter 1.5 cm., height 10 cm., eluting solution 200 ml.) to provide 1.5 g. (yield 79%) of oily 4-isopropyl-2-(7-indenyloxymethyl)morpholine.

Provenance & Evidence