Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 21024032, Verbindung

HRID 1446643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446643
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([O:26][CH:27]1[C:28]([O:70]C(OCC)C)([CH3:69])[CH2:29][CH2:30][CH:31]([O:63]C(OCC)C)[CH2:32][C:33]([O:35][CH:36](/[C:41](/[CH3:62])=[CH:42]/[CH:43]=[CH:44]/[CH:45]([CH3:61])[CH2:46][CH:47]2[O:60][CH:48]2[CH:49]([CH3:59])[CH:50]([O:53]C(OCC)C)[CH2:51][CH3:52])[CH:37]([CH3:40])[CH:38]=[CH:39]1)=[O:34])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CO>[C:18]([O:26][CH:27]1[C:28]([OH:70])([CH3:69])[CH2:29][CH2:30][CH:31]([OH:63])[CH2:32][C:33]([O:35][CH:36](/[C:41](/[CH3:62])=[CH:42]/[CH:43]=[CH:44]/[CH:45]([CH3:61])[CH2:46][CH:47]2[O:60][CH:48]2[CH:49]([CH3:59])[CH:50]([OH:53])[CH2:51][CH3:52])[CH:37]([CH3:40])[CH:38]=[CH:39]1)=[O:34])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 21024031HCID 21024031, Verbindung

Produkt 1

HCID 21024032HCID 21024032, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Pyridinium p-toluenesulfonate (2 mg, 7.5 μmol) was added to a solution of (8E,12E,14E)-7-benzoyloxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (6.1 mg, 7.48 μmol) in methanol (1 mL), followed by stirring at room temperature for one hour. The reaction solution was evaporated, ethyl acetate, water and a saturated sodium bicarbonate aqueous solution were added to the resulting residue, 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 thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=2:1) to obtain the title compound (3.3 mg, 74%) as a colorless oil.

Aufarbeitung

  1. customThe reaction solution was evaporated
  2. additionethyl acetate, water and a saturated sodium bicarbonate aqueous solution were added to the resulting residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6dbb1e6332ca488785453759934638c3
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667052B2

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