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Chlorotrimethylsilane → 1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

HRID 975058
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 975058
[CH3:1][C:2]1[N:3]=[CH:4][S:5][CH:6]=1.C([Li])CCC.C[Si](Cl)(C)C.[C:17]([C:20]1[CH:24]=[C:23]([CH3:25])[O:22][C:21]=1[CH3:26])(=[O:19])[CH3:18].C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:26][C:21]1[O:22][C:23]([CH3:25])=[CH:24][C:20]=1[C:17]([C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1])([OH:19])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 6397ChlorotrimethylsilaneHCID 127484-MethylthiazoleHCID 615273-Acetyl-2,5-dimethylfuranHCID 516892Sodium BicarbonateHCID 178418339Butyllithium2×

Produkt 1

HCID 189362891-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. temperatureAfter 30 minutes the mixture was again cooled to -70° C.
  3. temperatureto warm to room temperature
  4. waitAfter 30 minutes
  5. extractionthe mixture was extracted with diethylether
  6. washThe combined extracts were washed
  7. customdried
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-8a40174422a440fbb1fa16755cf0c042
Quelldatensatz
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05607956

Notizen zur Reaktion

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