Acetic Acid → (8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

HRID 1446637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446637
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH:11]1[C:12]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([CH3:53])[CH2:13][CH2:14][CH:15]([O:47][CH:48]([O:50][CH2:51][CH3:52])[CH3:49])[CH2:16][C:17]([O:19][CH:20](/[C:25](/[CH3:46])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:45])[CH2:30][CH:31]2[O:44][CH:32]2[CH:33]([CH3:43])[CH:34]([O:37][CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[CH2:35][CH3:36])[CH:21]([CH3:24])[CH:22]=[CH:23]1)=[O:18])(=O)C.C(O)(=O)C.C(OCC)(=O)C>CO.O>[CH2:51]([O:50][CH:48]([O:47][CH:15]1[CH2:14][CH2:13][C:12]([O:54][CH:55]([O:57][CH2:58][CH3:59])[CH3:56])([CH3:53])[CH:11]([OH:10])[CH:23]=[CH:22][CH:21]([CH3:24])[CH:20](/[C:25](/[CH3:46])=[CH:26]/[CH:27]=[CH:28]/[CH:29]([CH3:45])[CH2:30][CH:31]2[O:44][CH:32]2[CH:33]([CH3:43])[CH:34]([O:37][CH:38]([O:40][CH2:41][CH3:42])[CH3:39])[CH2:35][CH3:36])[O:19][C:17](=[O:18])[CH2:16]1)[CH3:49])[CH3:52]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21024001HCID 21024001, Verbindung

Produkt 1

HCID 21023947(8E,12E,14E)-3,6,21-Tri(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olideAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Potassium carbonate (138 mg, 0,996 mmol) was added to a solution of (8E,12E,14E)-7-acetoxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (250 mg, 0.332 mmol) in methanol (5 mL) at room temperature, followed by stirring at the same temperature for 2 hours. Acetic acid (60 mg, 1 mmol), ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, spherical, neutral, 40 to 50 μm, ethyl acetate-hexane=1:2 and 1:1, successively) to obtain the title compound (242 mg, 100%) as a colorless oil.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N

Quellen und Nachweise

ORD-Eintrag
ord-bcb1d3ce826a4efaa131b6ff38b3f06e
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667052B2

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