Dimethyl Sulfoxide → 2-Methyl-5-(oxiran-2-yl)pyridine

HRID 1401417Notes

Reaction equation

HRID 1401417 reaction equation
CS(C)=O.[H-].[Na+].[I-].[CH3:8][S+](C)C.[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][N:14]=1>C1COCC1>[CH3:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]2[CH2:8][O:18]2)=[CH:15][N:14]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 101925666-Methyl-3-pyridinecarboxaldehyde

Product 1

HCID 157135882-Methyl-5-(oxiran-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

DMSO is added to NaH 60% dispersion in oil (1-1.8 equiv.) and heated to 65° C. for 1 h. THF is added to the mixture at the same temperature and heated for another 10 min. After 10 min., the reaction mixture is cooled to 0° C. Trimethylsulfonium iodide (1-1.2 equiv.) is added and the contents are stirred for 10 min. A solution of 6-methylnicotinaldehyde (1 equiv.) in THF is added dropwise. After complete addition, the reaction mixture is stirred at RT for 2 h, and monitored by LCMS. The reaction mixture is poured in ice water, extracted in diethyl ether, dried over sodium sulfate and concentrated at 25° C. to get crude product 2-methyl-5-(oxiran-2-yl)pyridine.

Workup

  1. temperatureheated for another 10 min
  2. temperaturethe reaction mixture is cooled to 0° C
  3. additionAfter complete addition
  4. stirringthe reaction mixture is stirred at RT for 2 h
  5. extractionextracted in diethyl ether
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated at 25° C.

Sources & evidence

ORD record
ord-ea7a2928cc2841cd842d8a2f4547a57a
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

Loading…