3,4-dihydro-2H-pyran → HCID 10986966, compound

Participants

Reaction Steps

Ten milligrams of (S)-trans-3,5-dihydroxycyclopent-1-ene and 8 milligrams of dihydropyran were stirred at room temperature for 24 hours in 1.0 milliliter of methylene chloride in the presence of 0.1 milligram of p-toluenesulfonic acid. Next, the organic solution was washed with an aqueous sodium bicarbonate solution and then with an aqueous sodium chloride solution, after which it was dried with anhydrous magnesium sulfate followed by distilling off the solvent under reduced pressure. When the resulting crude product was purified by thin-layer chromatography (n-hexane:ethyl acetate = 6:4), 10 milligrams (54%) of (S)-trans-5-tetrahydropyranyloxycyclopent-1-en-3-ol was obtained. The IR and NMR of this product was in complete agreement with those of the product obtained in Example 36.

Provenance & Evidence