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

HRID 1400342Notes

Reaction equation

HRID 1400342 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)pyridineYield 137.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

DMSO (4 mL) was added to NaH 60% dispersion in oil (0.314 g, 7.8 mmol, 1.3 eq.) and heated it to 65° C. for 1 h. THF (10 mL) was added at the same temperature and heated for another min. After 10 min, reaction mixture was cooled to 0° C. Trimethylsulfonium iodide (1.2 g, 5.9 mmol, 1 eq.) was added and stirred for 10 min and solution of 6-methylnicotinaldehyde (0.720 g, 5.9 mmol, 1 eqv) in THF was added dropwise. After complete of addition, reaction mixture was stirred at RT for 2 h. Product was detected by LCMS. Reaction mixture was poured in ice water. Product was extracted in diethyl ether (4×50 mL), dried over sodium sulfate and concentrated under vacuum at 25° C. to get product 2-methyl-5-(oxiran-2-yl)pyridine (1.1 g).

Workup

  1. temperatureheated for another min
  2. customreaction mixture
  3. temperaturewas cooled to 0° C
  4. additionAfter complete of addition, reaction mixture
  5. stirringwas stirred at RT for 2 h
  6. customReaction mixture
  7. extractionProduct was extracted in diethyl ether (4×50 mL)
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum at 25° C.

Sources & evidence

ORD record
ord-3c41533aaa104fa58e086a1755b38313
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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