Triethylamine → HCID 20448808, Verbindung

HRID 358370

Reaktionsgleichung

Reaktionsgleichung von HRID 358370
[Si:1]([O:8][C@@H:9]1[CH2:13][C:12](=O)[CH:11]2[O:15][CH:10]12)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[SH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(N(CC)CC)C.[Cl-].[NH4+]>CO>[Si:1]([O:8][CH:9]1[CH2:10][C:11](=[O:15])[C:12]([S:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 5482614-Sulfanylbutan-1-olHCID 13362510HCID 13362510, Verbindung

Produkt 1

HCID 20448808HCID 20448808, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

2.80 g (12.2 mmoles) of 4(R)-t-butyldimethylsilyloxy-2,3-epoxycyclopentanone and 1.30 g (12.2 mmoles) of 4-mercaptobutan-1-ol were dissolved in 12 ml of methanol, and with stirring 1.87 ml (13.5 mmoles) of triethylamine was added. The stirring was continued for 30 minutes. Ten milliliters of a saturated aqueous solution of ammonium chloride was added, and the mixture was concentrated. The residue was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated. The resulting oily product was chromatographed on a silica gel column using hexane/ethyl acetate (8/1) as an eluent to give 3.12 g (81%) of 4(RS)-t-butyldimethylsilyloxy-2-(4-hydroxybutylthio)-2-cyclopentenone.

Aufarbeitung

  1. additionwas added
  2. concentrationthe mixture was concentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting oily product was chromatographed on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-50b7a521cf9c4e52b702724c63423584
Quelldatensatz
uspto-grants-1984_08
Patentnummer
US04466980

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