Diethyl Ether → 1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanol

HRID 860586Notes

Reaction equation

HRID 860586 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][C:7]=1[CH:8]=[O:9])[CH3:2].[CH3:20][Mg]Br.C(OCC)C>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][C:7]=1[CH:8]([OH:9])[CH3:20])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 587657044-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 587658011-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde (0.793 g, 2.95 mmole) in THF (30 mL) at 0° C., is added a solution of methyl magnesium bromide in diethyl ether (3.0M, 2.0 mL, 0.60 mmole) dropwise. The reaction is stirred for 5 minutes and then warmed up to room temperature for 30 minutes. The reaction is quenched with NH4Cl(aq) (10 mL), partitioned between ethyl acetate (50 mL) and water (50 mL). Extracted the aqueous layer with ethyl acetate (2×50 mL). The combined organic is washed with brine (3×100 mL), dried over Na2SO4, filtered and concentrated to provide the titled compound as a white solid. The crude product is used for the next step without further purification. Mass [EI+] 286 (M+H)+.

Workup

  1. customThe reaction is quenched with NH4Cl(aq) (10 mL)
  2. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionExtracted the aqueous layer with ethyl acetate (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-ddcb37fafce74f7d866b5505955fb75c
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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