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

HRID 1719721Notes

Reaction equation

HRID 1719721 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[C:9]([C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1)(=[O:11])[CH3:10]>C1COCC1>[CH3:10][C:9]1([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH2:4][O:11]1

Participants

5

Reactant 3

HCID 142824-AcetylpyridineHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (5.0 g of a 50% dispersion in oil) was added portionwise to a stirred suspension of trimethylsulphoxonium iodide (22.0 g) in THF (150 cm3) and the mixture was heated under reflux for 3 hours. After cooling to 40°, 4-acetyl-pyridine (10.0 g) was added and the mixture was again heated under reflux for 1 hour. The cooled mixture was evaporated in vacuo, partitioned between ether (100 cm3) and water (50 cm3) and the aqueous phase was further extracted with ether (2×50 cm3). The combined dried extracts were evaporated to afford 2-methyl-2-[4-pyridyl]oxirane as a crude oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling to 40°
  4. temperaturethe mixture was again heated
  5. temperatureunder reflux for 1 hour
  6. customThe cooled mixture was evaporated in vacuo
  7. custompartitioned between ether (100 cm3) and water (50 cm3)
  8. extractionthe aqueous phase was further extracted with ether (2×50 cm3)
  9. customThe combined dried extracts
  10. customwere evaporated

Sources & evidence

ORD record
ord-874882aaf0ad40c9ae80d686a0d0063b
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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