Dichloromethane → 4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde

HRID 860597Notes

Reaction equation

HRID 860597 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)[O:5][C:6]=1[CH2:7][OH:8].CC1N=C(C2C=CC(C(F)(F)F)=CC=2)OC=1C=O.ClCCl.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(=O)([O-])O.[Na+]>[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)[O:5][C:6]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 865981314-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde [4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol

Product 1

HCID 597859814-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde [4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-methanol (2.42 g, 9.41 mmol) and 100 mL dichloromethane are stirred at room temperature. Dess-Martin periodinane (8.0 g, 18.8 mmol) is added and the resulting mixture is stirred 4 hr at room temperature. The mixture is diluted with 100 mL saturated sodium hydrogen carbonate. The organic layer is separated, washed with 50 mL each of water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product is purified by silica gel chromatography eluting with a mixture of 8:2 hexanes:ethyl acetate affording 4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde as a white solid, 2.12 g, 89%. MS (M++1) 256.

Workup

  1. customThe organic layer is separated
  2. washwashed with 50 mL each of water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel chromatography
  7. washeluting with a mixture of 8:2 hexanes

Sources & evidence

ORD record
ord-ce9d7fa27fea475cbdca8cefeb6438ff
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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