4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehyde → HCID 21051236, Verbindung

HRID 490712

Reaktionsgleichung

Reaktionsgleichung von HRID 490712
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[S:5][C:6]=1[CH:7]=[O:8].[CH2:19]([Mg]Cl)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[S:5][C:6]=1[CH:7]([OH:8])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 178418336HCID 178418336, Verbindung

Produkt 1

HCID 21051236HCID 21051236, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde (0.5 g, 1.84 mmole) in THF (20 mL) at 0° C., is added a solution of benzyl magnesium chloride in tetrahedronfuran (2.0M, 1.0 mL, 2 mmole) dropwise. The reaction is stirred for 5 minutes and then warmed up to room temperature for 2 hrs. The reaction is quenched with NH4Cl(aq), partitioned between ethyl ether and water. Extracted the aqueous layer with ethyl ether. The combined organic is washed with brine, dried over Na2SO4, filtered and concentrated. Column chromatography on silica gel yields the title compound.

Aufarbeitung

  1. customThe reaction is quenched with NH4Cl(aq)
  2. custompartitioned between ethyl ether and water
  3. extractionExtracted the aqueous layer with ethyl ether
  4. washThe combined organic is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17690e186b7a41bd9e1cb2adbd460c52
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528160B2

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