HCID 86647042, compound → (2R)-5-hexyl-4-hydroxy-2-undecyl-2,3-dihydropyran-6-one

Participants

Reaction Steps

To improve the yield of (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one, U.S. Pat. Nos. 5,274,143 and 5,420,305 disclose a method involving intramolecular cyclization of (R)-3-[2-bromo-1-oxooctyloxy]-tetradecanoate in the presence of zinc to produce (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one in a yield of 61 to 67%, while U.S. Pat. No. 6,545,165 describes intramolecular cyclization of (R)-3-[2-bromo-1-oxooctyloxy]-tetradecanoate in the presence of tert-butyl magnesium chloride to produce (6R)-3-hexyl-4-hydroxy-6-undecyl-5,6-dihydropyran-2-one in a yield of 78%.

Provenance & Evidence