3,4-dihydro-2H-pyran → HCID 86737123, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.067 g of (13E)-(5RS,6RS,9α,11α,15RS)-5-iodo-6,9-epoxy-11,15-dihydroxy-15-methylprost-13-enoic acid methyl ester [prepared as described in Reference Example 2(c)] in 20 ml of methylene chloride were added 1.4 mg of p-toluenesulphonic acid and 1.337 g of 2,3-dihydropyran and the mixture was stirred at -4° C. for 4.5 hours. The reaction mixture was then neutralised with an aqueous solution of sodium bicarbonate and extracted with chloroform. The extract was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 1.2 g of the title compound having the following physical characteristics:

Provenance & Evidence