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

HRID 490712

Reaction equation

HRID 490712 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 21051236HCID 21051236, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-17690e186b7a41bd9e1cb2adbd460c52
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Linked notes

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