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

HRID 1267315Notes

Reaction equation

HRID 1267315 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.CCCCCC.C([Li])CCC.CN(C)[CH:36]=[O:37]>O1CCCC1>[CH:36]([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:37]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 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 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-iodo-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (2.5 g) in tetrahydrofuran (40 ml) was added dropwise, at −65° C. under nitrogen streams, a hexane solution of n-butyllithium (1.6M, 4.61 ml). The mixture was stirred for 15 minutes at the same temperature, to which was added dropwise N,N-dimethylformamide (0.71 ml). The cooling bath was removed, then the reaction mixture was stirred for further 30 minutes, to which was added a saturated aqueous solution of ammonium chloride (6 ml). The reaction mixture was poured into water, followed by extraction with ethyl acetate. The ethyl acetate was washed with water and dried (MgSO4), then the solvent was distilled off under reduced pressure to leave 5-formyl-2-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]pyridine (1.5 g, 79%). Recrystallization from ethyl acetate-hexane gave colorless crystals, m.p.99-100° C.

Workup

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred for further 30 minutes, to which
  3. additionwas added a saturated aqueous solution of ammonium chloride (6 ml)
  4. additionThe reaction mixture was poured into water
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe ethyl acetate was washed with water
  7. dry with materialdried (MgSO4)
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-48b46c6369f04071857dcb8f04eafb4e
Source dataset
uspto-grants-2003_04
Patent number
US06552058B1

Reaction notes

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