Sodium Hydroxide → HCID 19820412, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3.13 g of aluminum trichloride in 110 ml of diethyl ether was added to a suspension of 1.56 g lithium aluminum hydride in 110 ml of diethyl ether and then cooled to approx. 5° C., after which a solution of 4.27 g of ethyl 3-chloro-7,8,9,10-tetrahydro-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine-8-carboxylate 92 ml of tetrahydrofuran was slowly added. After 1 h the aluminum complex was decomposed by addition of 21 ml of 1N sodium hydroxide solution. After 30 min stirring the salts were removed with suction and rinsed with dichloromethane. After evaporation of the solvent 3.6 g of crude product was obtained, which was purified by silica chromatography with toluene-ethanol (9:1) to obtain pure 3-chloro-7,8,9,10-tetrahydro-8-methyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine. After conversion into the maleate and recrystallization from ethanol-diethylether 2.6 g (52%) of 3-chloro-7,8,9,10-tetrahydro-8-methyl-6H-dibenzo[b,j][1,4,7]dioxaazacycloundecine (Z)-2-butenedioate (1:1), mp 145°-157° C., was obtained.

Provenance & Evidence