Ethyl Acetate → HCID 86604546, Verbindung

HRID 1446644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446644
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C(OC(O[CH:17]1[CH2:29][CH2:28][C:27]([O:31][CH:32]([O:34][CH2:35][CH3:36])[CH3:33])([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH2:18]1)C)C.Cl.C(Cl)(=O)C1C=CC=NC=1.C(OCC)(=O)C>O1CCCC1.O1CC(CCN)C(CCN)C1CCN.O>[CH2:35]([O:34][CH:32]([O:31][C:27]1([CH3:30])[CH:26]([OH:37])[CH:25]=[CH:24][CH:23]([CH3:38])[CH:22](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:21][C:19](=[O:20])[CH:18]=[CH:17][CH2:29][CH2:28]1)[CH3:33])[CH3:36]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 2733832Lithium HexamethyldisilazideHCID 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-olide

Produkt 1

HCID 86604546HCID 86604546, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 68666183HCID 68666183, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium bis(trimethylsilyl)amide (1.0 M tetrahydrofuran solution, 50 μL, 50 μmol) was added dropwise to a solution of (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 (10.8 mg, 15.2 μmol) in tetrahydrofuran (2 mL) at −40° C. under nitrogen atmosphere, followed by stirring at the same temperature for 20 min. Then, a solution of nicotinoyl chloride hydrochloride (5.7 mg, 30.4 μmol) in tetrahydrofuran-triethylamine (tetrahydrofuran: 0.5 mL and triethyamine: 1 drop) was added dropwise thereinto, followed by stirring at 0° C. for 30 min. Ethyl acetate and water were added to the reaction solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4) to obtain the title compound (6.3 mg, 67%) as a colorless oil.

Aufarbeitung

  1. stirringby stirring at 0° C. for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-3e2c924abf374222ab56b653f2426e6e
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667052B2

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