Dimethyl Sulfoxide → 3-(Oxiran-2-yl)pyridine

HRID 1481379Notes

Reaction equation

HRID 1481379 reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>C1COCC1>[O:19]1[CH2:8][CH:12]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 103713-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 133195613-(Oxiran-2-yl)pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

The title compound was prepared by following general procedure 3. Sodium hydride 50% dispersion in oil (1.64 g, 34.2 mmol, 1.8 equiv.) was taken into DMSO (12 mL) and heated at 65° C. for 1 h. THF (36 mL) was added at the same temperature and heated for 10 min. The reaction mixture was cooled to 0° C. and trimethylsulfonium iodide (3.81 g, 18.6 mmol, 1 equiv.) was added, followed by nicotinaldehyde (2 g, 18.6 mmol, 1 equiv.) and stirred at RT for 1 h. The reaction was monitored by TLC and LCMS. After completion of the reaction, the reaction mixture was poured in ice and extracted with diethyl ether, dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford 3-(oxiran-2-yl)pyridine (1 g).

Workup

  1. customThe title compound was prepared
  2. temperatureheated for 10 min
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customAfter completion of the reaction
  5. additionthe reaction mixture was poured in ice
  6. extractionextracted with diethyl ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1f573154fa4c47b4a5f21e7806a37eec
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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