6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo(c)chromen-1-ol → 1-[4-(Morpholino)butyryloxy]-3-n-pentyl-6,6,9-trimethyl-10a,6a,7,8-tetrahydrodibenzo[b,d]pyran hydrochloride

Participants

Reaction Steps

0.7 g. (2.23 mmoles) of 1-Hydroxy-3 n-pentyl-6,6,9-trimethyl-6a,7,8,10 a-tetrahydrodibenzo[ b,d]pyran, 0.48 g. (2.28 mmoles) of γ-morpholinobutyric acid hydrochloride (Cruickshank and Sheehan, J. Am. Chem. Soc. 83, 2891 (1961), m.p. 180°-182°C.) and 0.48 g. (2.35 mmoles) of dicyclohexylcarbodiimide were combined with 35 ml. of methylene chloride and stirred at room temperature for a total of 40 hours. The insoluble by-product of dicyclohexylurea was separated by filtration and the methylene chloride was removed using a rotary evaporator. The resulting residue was dissolved in about 20 ml. of benzene and a small amount of insoluble material was removed by filtration. The benzene was evaporated and the residue dried in vacuo to give 0.7 g. of fluffy, white material. Crystallization from benzene/petroleum ether gave 0.4 g. of product as colorless crystals, m.p. 99°-101°C. The material was pure by thin layer chromatography (10% MeOH/CHCl3); the infrared and nuclear magnetic resonance spectra were in agreement with the proposed structure.

Provenance & Evidence