N-Methyl-N-(pyridine-2-yl)formamide → 4,5-Diphenyloxazole-2-carbaldehyde

HRID 868920Notes

Reaction equation

HRID 868920 reaction equation
[Li]CCCC.[C:6]1([C:12]2[N:13]=[CH:14][O:15][C:16]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C1C=CC=CN=1)[CH:25]=[O:26]>C1COCC1>[C:6]1([C:12]2[N:13]=[C:14]([CH:25]=[O:26])[O:15][C:16]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 572611N-Methyl-N-(pyridine-2-yl)formamideHCID 6134984,5-DiphenyloxazoleHCID 178418339Butyllithium

Product 1

HCID 183673414,5-Diphenyloxazole-2-carbaldehydeYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-BuLi (361 mg, 5.65 mmol) was added to a stirred and cooled (−78° C.) solution of 4,5-diphenyloxazole (500 mg, 2.26 mmol) in dry THF. The stirring was continued for 30 min at −78° C., and N-methyl-N-(pyridin-2-yl)formamide (461 mg, 3.39 mmol) was added. The resulting solution was stirred at −78° C. for 1 h, then quenched with H2O. The mixture was extracted with EtOAc (3×20 mL), and the combined organic extracts were dried (MgSO4) and concentrated. The crude product was purified by column chromatography to afford the desired product 4,5-diphenyloxazole-2-carbaldehyde (372 mg) as an orange oil.

Workup

  1. stirringThe resulting solution was stirred at −78° C. for 1 h
  2. customquenched with H2O
  3. extractionThe mixture was extracted with EtOAc (3×20 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-c1bc63c1ecb5489d8283d5db9ef223c6
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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