Ethanol → HCID 86592488, Verbindung

HRID 460029

Reaktionsgleichung

Reaktionsgleichung von HRID 460029
[H-].[Na+].C(O)C.[Cl-].[CH2:7]([O:9][C:10](=[O:40])[CH2:11][O:12][C:13]1[CH:38]=[CH:37][C:16]([CH2:17][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:15][C:14]=1[CH3:39])[CH3:8].[CH3:41][C:42]1[N:43]=[C:44]([C:49]2[CH:54]=[CH:53][C:52]([C:55]([F:58])([F:57])[F:56])=[CH:51][CH:50]=2)[S:45][C:46]=1[CH:47]=O>O>[CH2:7]([O:9][C:10](=[O:40])[CH2:11][O:12][C:13]1[CH:38]=[CH:37][C:16]([CH:17]=[CH:47][C:46]2[S:45][C:44]([C:49]3[CH:50]=[CH:51][C:52]([C:55]([F:58])([F:56])[F:57])=[CH:53][CH:54]=3)=[N:43][C:42]=2[CH3:41])=[CH:15][C:14]=1[CH3:39])[CH3:8]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde2×HCID 16109177HCID 16109177, Verbindung2×

Produkt 1

HCID 86592488HCID 86592488, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydride (0.040 g, 60% dispersion in mineral oil) was added to anhydrous ethanol (20 ml) followed by [4-(2-ethoxy-2-oxoethoxy)-3-methylbenzyl](triphenyl)phosphonium chloride (intermediate 18, 0.45 g) after 10 minutes. After a further 10 minutes 4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde (intermediate 2, 0.24 g) was added and the reaction mixture stirred at ambient temperature for 3 hours. The reaction mixture was treated with water and then the mixture extracted with chloroform. The chloroform solution was separated with a hydrophobic frit and excess aldehyde removed using 3-[4-(hydrazinosulfonyl)phenyl]propionyl AM resin (0.50 g). The crude product remaining after this treatment was purified by Biotage™ chromatography using a mixture of petroleum ether:ethyl acetate (5:1) as eluent to give the title compound as a mixture of E and Z isomers.

Aufarbeitung

  1. extractionthe mixture extracted with chloroform
  2. customThe chloroform solution was separated with a hydrophobic frit and excess aldehyde
  3. customremoved
  4. customwas purified by Biotage™ chromatography
  5. additiona mixture of petroleum ether:ethyl acetate (5:1) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-9e71b5a9e3f240a0886e6c872cbe7695
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196107B2

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