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

HRID 233274Notes

Reaction equation

HRID 233274 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. in nitrogen streams, a hexane solution of n-butyl lithium (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, and 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, which was subjected to extraction with ethyl acetate. The ethyl acetate layer 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%), which was recrystallized from ethyl acetate--hexane to give 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, which
  5. extractionwas subjected to extraction with ethyl acetate
  6. washThe 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-53ada4e6a2ea47baa095cb6c6d83f8a7
Source dataset
uspto-grants-1997_01
Patent number
US05591862

Reaction notes

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