Diethyl Ether → 1-[4-Methyl-2-(4-trifluoromethylphenyl)thiazol-5-yl]ethanol

HRID 860588Notes

Reaction equation

HRID 860588 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].[CH3:19][Mg]Br.C(OCC)C>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])[CH3:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27828994-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 226476311-[4-Methyl-2-(4-trifluoromethylphenyl)thiazol-5-yl]ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carbaldehyde (1.5 g, 5.53 mmole) in THF (50 mL) at 0° C., is added a solution of methyl magnesium bromide in diethyl ether (3.0M, 2.0 mL, 6.0 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) (10 mL), partitioned between ethyl ether (50 mL) and water (50 mL). Extracted the aqueous layer with ethyl ether (2×50 mL). The combined organic is washed with brine (3×100 mL), dried over Na2SO4, filtered and concentrated. Column chromatography on silica gel gave 1.35 gram of the title compound.

Workup

  1. customThe reaction is quenched with NH4Cl(aq) (10 mL)
  2. custompartitioned between ethyl ether (50 mL) and water (50 mL)
  3. extractionExtracted the aqueous layer with ethyl ether (2×50 mL)
  4. washThe combined organic is washed with brine (3×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f18aaa4f3c26473ea4791530805867bd
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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