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

HRID 885767Notes

Reaction equation

HRID 885767 reaction equation
Br[CH:2]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:3](=[O:21])[O:4][C@H:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:6][C:7]([O-:9])=O.C([Mg]Cl)(C)(C)C>>[CH2:22]([C:2]1[C:3](=[O:21])[O:4][C@H:5]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:6][C:7]=1[OH:9])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

3

Reactant 2

HCID 86647042HCID 86647042, compoundHCID 178418310HCID 178418310, compound

Product 1

HCID 54690023(2R)-5-hexyl-4-hydroxy-2-undecyl-2,3-dihydropyran-6-oneYield 78%

Procedure

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%.

Sources & evidence

ORD record
ord-1a50edd51dfc4ffd824d2830f453c97e
Source dataset
uspto-grants-2012_08
Patent number
US08242288B2

Reaction notes

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