Sodium hydride → 2-tert.-Butyl-2-[(4-chlorophenoxy)-fluoromethyl]-oxirane

HRID 64769Notes

Reaction equation

HRID 64769 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Cl:9][C:10]1[CH:24]=[CH:23][C:13]([O:14][CH:15]([F:22])[C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][CH:11]=1>CS(C)=O.C1COCC1>[C:17]([C:16]1([CH:15]([O:14][C:13]2[CH:12]=[CH:11][C:10]([Cl:9])=[CH:24][CH:23]=2)[F:22])[CH2:2][O:21]1)([CH3:19])([CH3:20])[CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13078445HCID 13078445, compound

Product 1

HCID 202353632-tert.-Butyl-2-[(4-chlorophenoxy)-fluoromethyl]-oxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

43 g of trimethyloxosulfonium iodide were added in portions to a dispersion of 5.28 g of 80% sodium hydride in 300 ml of absolute DMSO under a nitrogen atmosphere, while stirring. When the exothermic reaction had subsided, the mixture was stirred for a further 1 h, a solution of 40 g of 1-(4-chlorophenoxy)-3,3-dimethyl-1-fluoro-2-butanone in 100 ml of THF was then added dropwise at RT and the mixture was stirred at RT for a further 2 h. The reaction solution was then poured onto ice-water and extracted several times with diethyl ether. The combined extracts were washed with water, dried over sodium sulfate and filtered and the filtrate was concentrated. Yield of crude product: 41.5 g in the form of a yellow-brown oil, which can be either purified by column chromatography or further processed without purification.

Workup

  1. customWhen the exothermic reaction
  2. stirringthe mixture was stirred for a further 1 h
  3. stirringthe mixture was stirred at RT for a further 2 h
  4. additionThe reaction solution was then poured onto ice-water
  5. extractionextracted several times with diethyl ether
  6. washThe combined extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customeither purified by column chromatography
  11. customfurther processed without purification

Sources & evidence

ORD record
ord-3243b25a88264483a68c8a025f5f854e
Source dataset
uspto-grants-1986_09
Patent number
US04610716

Reaction notes

Loading…