1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanone → 2-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol

HRID 860682Notes

Reaction equation

HRID 860682 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:5][C:6]=1[C:7](=[O:9])[CH3:8].[CH3:20][Mg]Br>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:5][C:6]=1[C:7]([OH:9])([CH3:20])[CH3:8]

Participants

4

Reactant 2

HCID 213009531-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 695893092-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanone (0.58 g, 2.15 mmol) is stirred in tetrahydrofuran (25 mL) at zero deg. C. Methyl magnesium bromide (1.1 mL, 3.23 mmol, 3 M in ether) is added and the reaction stirred at room temperature 2 hr. The mixture is cooled on ice/water and quenched with saturated ammonium chloride (5 mL). The product is extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to afford the product as a tan solid, 0.40 g, 65%). MS M++1 286. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. temperatureThe mixture is cooled on ice/water
  2. customquenched with saturated ammonium chloride (5 mL)
  3. extractionThe product is extracted with ethyl acetate (3×50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b24b7862f1c3429baf0974f3fc7bc2c1
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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