Pyridine → HCID 86747421, compound

Participants

Reaction Steps

(1S, 4aS, 7S, 7aR)-4-(acetoxymethyl)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-7-methylcyclopenta[c]pyran (40.0 g, 0.135 mol) obtained in Example 6 was dissolved in 1,000 ml of ethyl acetate. After 20 ml of pyridine was added, 10% palladium carbon (1.2 g) was suspended in the reaction solution, and this solution was stirred for 48 hours in a hydrogen gas atmosphere of 1 atm. After the catalyst was removed by celite filtration, 1,000 ml of ethyl acetate was added, and this organic layer was washed with 2N hydrochloric acid solution (1,000 ml) and saturated sodium chloride solution (1,000 ml). The organic layer was dried by magnesium sulfate, and was filtered, and then concentrated under a reduced pressure. The residual matter was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=8:2 eluent was distilled off. A colorless oily substance was thus obtained, i.e., (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethyl-cyclopenta[c]pyran (29.5 g, yield=93.1%). This (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-1, 4a, 5, 6, 7, 7a-hexahydro-4, 7-dimethylcyclopenta[c]pyran had the following physicochemical properties:

Provenance & Evidence