Water → HCID 58453198, compound

HRID 2109529Notes

Reaction equation

HRID 2109529 reaction equation
CS(O[CH:6]([CH:18]1[CH2:20][CH2:19]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=O)=O.C([O-])(C)(C)C.[K+].O>CN(C)C=O>[N+:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH:8]1[CH2:7][CH:6]1[CH:18]1[CH2:20][CH2:19]1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 866212421-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

Product 1

HCID 58453198HCID 58453198, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.18 g of 1-cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate (3.94 mmol) is dissolved in 40 ml of dimethylformamide, 0.91 g of potassium tert-butanolate (97%, 7.88 mmol) are added and stirring is carried out for 1 hour at ambient temperature under a nitrogen atmosphere. Water is added to the reaction mixture. Extraction is carried out with ethyl acetate, and the organic phase is dried over sodium sulfate and concentrated by evaporation. Chromatography on silica gel is carried out in order to remove by-products (eluant: ethyl acetate/hexane 1:2). After removal of the eluant, 0.68 g of 2-(2-nitrophenyl)-bicyclopropane (85% of theory) is obtained in the form of an orange-coloured liquid (trans:cis ratio: 6.5:1).

Workup

  1. extractionExtraction
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customto remove by-products (eluant: ethyl acetate/hexane 1:2)
  5. customAfter removal of the eluant

Sources & evidence

ORD record
ord-d027c83575c5456fb94f68fc0fce9e12
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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