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Acetic Acid → 2-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone

HRID 1197040
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1197040
[CH3:1][S-:2].[Na+].C(O)(=O)C.C(N(CC)CC)C.O1[CH:20]2[CH:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]2[CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CO.O>[CH3:1][S:2][C:16]1[C:17](=[O:48])[CH:18]([CH:37]([OH:47])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43]([O:45][CH3:46])=[O:44])[CH:19]([CH:21]=[CH:22][CH:23]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:20]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 54508019HCID 54508019, Verbindung

Produkt 1

HCID 572430522-Methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenoneAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium thiomethoxide (2.30 g) in methanol (100 ml) was cooled to 0° C., acetic acid (2.82 ml) was added, the mixture was stirred for 5 minutes, Triethylamine (915 ml) was added, and a solution of 2,3-epoxy-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)cyclopentanone (3.26 g) in methanol (40 ml) was added. After stirring at room temperature for 12 hours, water was added to the mixture, and the mixture extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered, followed by concentration. The concentrate was subjected to silica gel chromatography to give 3.47 g (yield 96%) of 2-methylthio-5-(1-hydroxy-6-methoxycarbonylhexyl)-4-(3-t-butyldimethylsilyloxy-1-octenyl)-2-cyclopentenone.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 12 hours
  2. extractionthe mixture extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationfollowed by concentration

Quellen und Nachweise

ORD-Eintrag
ord-5c33214236fd4aa9ac726f779b0af62a
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05116869

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