Toluene → 2-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinaldehyde

HRID 1294218Notes

Reaction equation

HRID 1294218 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[N:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]#N)[O:17][N:16]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].C(OCC)(=[O:51])C>CCCCCC>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:22]2[N:29]=[CH:28][CH:27]=[CH:26][C:23]=2[CH:24]=[O:51])[O:17][N:16]=1

Participants

7

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 688861452-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

Product 1

HCID 865915712-[[3-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile (2.60 g) and anhydrous toluene (100 mL) was dropwise added a solution (0.95 M, 15.5 mL) of diisobutylaluminum hydride in hexane at −78° C. The reaction mixture was allowed to warm to room temperature with stirring for 1.5 hrs. A saturated aqueous ammonium chloride solution (30 mL) was dropwise added to the mixture and the mixture was further stirred at room temperature for 30 min. Ethyl acetate was added to the mixture and the mixture was washed with saturated aqueous ammonium chloride solution and then with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (1.70 g, 65%) of 2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinaldehyde from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 90-91° C.

Workup

  1. stirringthe mixture was further stirred at room temperature for 30 min
  2. washthe mixture was washed with saturated aqueous ammonium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4dbcfb3763e34f5b867392557b769c05
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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