Dicyclohexylcarbodiimide → 1-[4-(Thiomorpholino)butyryloxy]-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[b,d] pyran

Participants

Reaction Steps

A mixture of 4.0 g. (10.8 mmole) of 1-hydroxy-3-(3-methyl-2-octyl)-6,6,9-trimethyl-7,8,9,10-tetrahydro-6H-dibenzo[ b,d] pyran, 2.4 g. (10.8 mmole) of γ-thiomorpholinobutyric acid hydrochloride, 2.38 g. (11.5 mmole) of dicyclohexylcarbodiimide and 250 ml. of methylene chloride was stirred and heated at reflux for 18 hours. After cooling the reaction mixture, the byproduct of dicyclohexylurea was removed by suction filtration. The solvent was evaporated to give a red-brown residue which was chromatographed using 90 g. of activated magnesium silicate (60-100 mesh) and chloroform as the solvent system. The fractions were monitored by thin layer chromatography, and the appropriate fractions were combined and evaporated to give 1.0 g. of a light yellow oil. The material was pure by thin layer chromatography, and the infrared and nuclear magnetic resonance spectra were in agreement with the designated structure.

Provenance & Evidence