Dichloromethane → 3-(3-Methyl-2-octyl)-1-[4-(morpholino)butyryloxy]-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran hydrobromide

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Reaction Steps

4.12 g. (11.15 mmole) of 1-Hydroxy-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d]pyran was combined with 2.84 g. (11.15 mmole) of γ-morpholinobutyric acid hydrobromide and 2.48 g. (12.0 mmole) of dicyclohexylcarbodiimide in 250 ml. of methylene chloride and stirred at room temperature for 16 hours. The by-product of dicyclohexylurea was removed by filtration and the filtrate was evaporated to give a golden, viscous residue. The material was dissolved in ether and the solid which appeared was removed by filtration. Recrystallization from benzene/ether gave 2.8 g. (41%) of product as colorless crystals, m.p. 120°-122°. The compound showed an Rf 0.7 in 10 % MeOH/CHCl3 ; the infrared and nmr spectra are consistent with the proposed structure.

Provenance & Evidence