4-Acetylpyridine → 4-(2-Methyloxiran-2-yl)pyridine

HRID 1401571Notes

Reaction equation

HRID 1401571 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[C:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)(=[O:10])[CH3:9]>CN(C=O)C.CS(C)=O>[CH3:9][C:8]1([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH2:2][O:10]1

Participants

6

Reactant 3

HCID 142824-AcetylpyridineHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 123953864-(2-Methyloxiran-2-yl)pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Trimethylsulfonium iodide (43.8 g, 210 mmol) was dissolved in 100 mL DMF and NaH (19.8 g, 495 mmol) was added. The reaction mixture was stirred for 5 min. and a solution of 4-acetylpyridine (20 g, 165 mmol) in 20 mL DMSO was added dropwise at RT. After the addition was complete, reaction mixture was stirred at RT for 2 h after which it was poured into ice water. The product was extracted with EtOAc, organic layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure. Yield: 21 g.

Workup

  1. additionAfter the addition
  2. customreaction mixture
  3. stirringwas stirred at RT for 2 h after which it
  4. extractionThe product was extracted with EtOAc, organic layer
  5. washwas washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-776df90714a04d279ff73878dad33af4
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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