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Thioguaiacol → HCID 21055320, Verbindung

HRID 2215270
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2215270
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[H-].[Na+].C1(C)C=CC(S([O:21][CH2:22][C@@H:23]([CH2:26][CH3:27])[CH2:24]O)(=O)=O)=CC=1>CN(C)C=O>[CH2:26]([C@H:23]([CH2:24][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[CH2:22][OH:21])[CH3:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 23642ThioguaiacolHCID 24758Sodium hydrideHCID 21055323HCID 21055323, Verbindung

Produkt 1

HCID 21055320HCID 21055320, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.47 ml (0.0038 mol) of 2-methoxythiophenol, in solution in 5 ml of dimethylformamide, is added dropwise to a round-bottomed flask, kept under an inert atmosphere, comprising 0.19 g (0.0047 mol) of sodium hydride in suspension in 10 ml of dimethylformamide cooled to 0° C. The mixture is reheated to ambient temperature and stirred for 1 hour, then 0.99 g (0.0038 mol) of 2-(S)-ethyl-3-hydroxypropyl p-toluene-sulfonate (XIXd-1), in solution in 10 ml of dimethyl-formamide, is added. After stirring at ambient temperature for 2 hours, the dimethylformamide is evaporated under high vacuum and the residue is taken up in dichloromethane. The organic phase is washed with water and with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2). 0.87 g (0.0038 mol) of the title compound (XXd-1) is recovered in the form of an oil.

Aufarbeitung

  1. customis reheated to ambient temperature
  2. stirringAfter stirring at ambient temperature for 2 hours
  3. customthe dimethylformamide is evaporated under high vacuum
  4. washThe organic phase is washed with water and with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/methanol=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-100010604e0e4f21884f198001f55dc5
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109234B2

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