Dimethylformamide → 6-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine-3-carbaldehyde

HRID 2395700Notes

Reaction equation

HRID 2395700 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1.C([Li])CCC.CN(C)[CH:30]=[O:31]>O1CCCC1.CCCCCC>[CH:30]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][C:11]2[N:12]=[C:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:14][C:15]=2[CH3:16])=[N:6][CH:7]=1)=[O:31]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 185461685-Iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridineHCID 178418339Butyllithium

Product 1

HCID 185461516-[2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]pyridine-3-carbaldehydeYield 79%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl) ethoxy]pyridine (2.5 g) in tetrahydrofuran (40 ml), a solution of n-butyl lithium in hexane (1.6M, 4.61 ml) was added dropwise at -65° C. in a nitrogen stream. After the mixture was stirred at the same temperature for 15 minutes, N,N-dimethylformamide (0.71 ml) was added dropwise. After the cooling bath was removed and the mixture was stirred for 30 more minutes, a saturated aqueous solution of ammonium chloride (6 ml) was added. The reaction mixture was poured into water and extracted with ethyl acetate. After the ethyl acetate layer was washed with water and dried (MgSO4), the solvent was distilled off under reduced pressure, to yield 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (1.5 g, 79%), which was then recrystallized from ethyl acetate-hexane to yield a colorless crystal.

Workup

  1. customAfter the cooling bath was removed
  2. stirringthe mixture was stirred for 30 more minutes
  3. additiona saturated aqueous solution of ammonium chloride (6 ml) was added
  4. additionThe reaction mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. washAfter the ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb4af44c373a4d5092b10abbce4bc37a
Source dataset
uspto-grants-1996_02
Patent number
US05489602

Reaction notes

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