Water → (S)-2-((2-Nitrophenoxy)methyl)oxirane

HRID 2223428Notes

Reaction equation

HRID 2223428 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[F-].[Cs+].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:17][C@H:18]1[O:20][CH2:19]1)(=O)=O.O>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:17][C@H:18]1[O:20][CH2:19]1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 69472-NitrophenolHCID 25953Cesium fluorideHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoate

Product 1

HCID 12619675(S)-2-((2-Nitrophenoxy)methyl)oxiraneYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Nitrophenol (0.92 g, 6.6 mmol) was dissolved in 5 ml anhydrous DMF. Cesium fluoride (3.02 g, 19.9 mmol) was added to the reaction. The reaction mixture was stirred for 1 hour at room temperature and (S)-glycidyl nosylate (1.71 g, 6.6 mmol) was added. The reaction was stirred for 16 hours at room temperature. Water (150 ml) was added, and the solution was extracted with ethylacetate. The organic phase was dried over MgSO4 and evaporated. The residue was purified with column chromatograph using ethylacetate:hexane (50:50) solvent to give (S)-glycidyl o-nitrophenyl ether (1.21 g, 90% yield, m.p. 46-47° C.) as a white solid.

Workup

  1. stirringThe reaction was stirred for 16 hours at room temperature
  2. extractionthe solution was extracted with ethylacetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated
  5. customThe residue was purified with column chromatograph

Sources & evidence

ORD record
ord-a9ae13c2975a4d6aa625cf7526d05244
Source dataset
uspto-grants-2008_05
Patent number
US07375136B2

Reaction notes

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