Tetrahydrofuran → 3-(Oxiran-2-yl)pyridine

HRID 1401422Notes

Reaction equation

HRID 1401422 reaction equation
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[I-].C[S+](C)C.[CH:13](=O)[C:14]1C=CC=[N:16][CH:15]=1>CS(C)=O>[O:6]1[CH2:5][CH:7]1[C:3]1[CH:4]=[N:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 103713-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodide

Product 1

HCID 133195613-(Oxiran-2-yl)pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride 50% dispersion in oil (1-1.8 equiv.) is taken in DMSO and heated at 65° C. for 1 h. THF is added to at the mixture at the same temperature and heated for 10 min. The reaction mixture is cooled to 0° C. and Trimethylsulfonium iodide (1-1.2 equiv.) is added, followed by nicotinaldehyde (1 equiv.) and the contents are stirred at RT for 1 h. The reaction is monitored by TLC and LCMS. After completion of the reaction, the reaction mixture is poured in ice and extracted with diethyl ether, dried over anhydrous sodium sulfate and evaporated under reduced pressure to afford crude product (3-(oxiran-2-yl)pyridine).

Workup

  1. temperatureheated for 10 min
  2. temperatureThe reaction mixture is cooled to 0° C.
  3. customAfter completion of the reaction
  4. additionthe reaction mixture is poured in ice
  5. extractionextracted with diethyl ether
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customto afford crude product (3-(oxiran-2-yl)pyridine)

Sources & evidence

ORD record
ord-c6076aefe43d425f9c63c685a7f50c80
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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