Iodine → HCID 53975217, compound

Participants

Reaction Steps

A suspension of zinc-copper couple (1.0 g.) (prepared by the method of R.S. Shank and H. Schechter, J. Org. Chem. (1959), 24, 1825) in diiodomethane (4.0 g.) and dry diethyl ether (10 ml.) was refluxed with a crystal of iodine for 0.5 hours. To the resulting suspension was added methyl 7-[2-hydroxy-5-(3-hydroxy-1-octenyl)cyclopentyl]heptanoate (1.0 g.) [prepared as described in Example 5] in dry diethyl ether (10 ml.) and the resulting mixture was refluxed for 24 hours. Addition of saturated ammonium chloride broke up the complex formed and the remaining zinc-copper couple was removed by filtration. The filtrate was separated and the diethyl ether layer dried over magnesium sulphate and evaporated to give methyl 7-[2-hydroxy-5-(3-hydroxy-1,2-methylene-1-octyl)cyclopentyl]heptanoate (1.04 g.). This was purified by preparative thin layer chromatography using the system employed in Example 10,νmax 3400 cm-1, 1730 cm-1 and 1170 cm-1.

Provenance & Evidence