Water → 2-(3,4-Diethoxyphenyl)-4-styrylthiazole

HRID 1489251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1489251
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[S:19][CH:20]=[C:21]([CH:23]=O)[N:22]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH3:7].O.C(OCC)(=O)C.O1C[CH2:35][CH2:34][CH2:33]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:18]2[S:19][CH:20]=[C:21]([CH:23]=[CH:4][C:3]3[CH:35]=[CH:34][CH:33]=[CH:1][CH:2]=3)[N:22]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH2:16][CH3:17])[CH3:7]

Komponenten

7

Edukt 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 187072072-(3,4-Diethoxyphenyl)-4-formylthiazoleHCID 178418339Butyllithium

Produkt 1

HCID 539918722-(3,4-Diethoxyphenyl)-4-styrylthiazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 70671Benzyltriphenylphosphonium chlorideKatalysator

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

4.2 ml of n-butyllithium was dropwise added in small portions to a suspension of 2.6 g of benzyltriphenylphosphonium chloride in 10 ml of tetrahydrofuran, with stirring at -50° C. The mixture was heated to room temperature and, after cooling again to -50° C., was mixed with 12 ml of a tetrahydrofuran solution of 2 g of 2-(3,4-diethoxyphenyl)-4-formylthiazole. The mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours. 10 ml of water and 40 ml of ethyl acetate were added to conduct extraction and phase separation. The solvent layer was dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography to obtain 2 g of 2-(3,4-diethoxyphenyl)-4-styrylthiazole as a 1:1 mixture of cis form and trans form.

Aufarbeitung

  1. temperatureThe mixture was heated to room temperature
  2. temperatureafter cooling again to -50° C.
  3. stirringThe mixture was stirred at the same temperature for 30 minutes and at room temperature for 14 hours
  4. extractionextraction and phase separation
  5. customThe solvent layer was dried
  6. distillationsubjected to distillation
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b9784346ad6e4544bd81b6580dc32da1
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677319

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