Water → (S)-2-((3-Nitrophenoxy)methyl)oxirane

HRID 2223425Notes

Reaction equation

HRID 2223425 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([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:5]=[C:6]([O:10][CH2:17][C@H:18]2[O:20][CH2:19]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 111373-NitrophenolHCID 25953Cesium fluorideHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoate

Product 1

HCID 7036817(S)-2-((3-Nitrophenoxy)methyl)oxiraneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Nitrophenol (0.92 g, 6.6 mmol) was dissolved in 5 ml anhydrous DMF, and cesium fluoride (3.02 g, 19.9 mmol) was added. 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 mixture was stirred for 20 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 m-nitrophenyl ether (1.02 g 80% yield, m.p 44-5° C.) as a yellowish solid.

Workup

  1. stirringThe reaction mixture was stirred for 20 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-7afe6c6a1ca9466f85b895378993647f
Source dataset
uspto-grants-2008_05
Patent number
US07375136B2

Reaction notes

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