Water → HCID 58453198, compound

HRID 2109530Notes

Reaction equation

HRID 2109530 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>CS(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, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.06 g of 1-cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate (3.54 mmol) is dissolved in 20 ml of dimethyl sulfoxide, 1.05 g of potassium tert-butanolate (97%, 10.62 mmol) are added, and stirring is carried out for 1.5 hours 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 1:10). After removal of the eluant, 0.68 g of 2-(2-nitrophenyl)-bicyclopropane (67% of theory) are obtained in the form of an orange-coloured liquid (trans:cis ratio: 7.7:1).

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 1:10)
  5. customAfter removal of the eluant, 0.68 g of 2-(2-nitrophenyl)-bicyclopropane (67% of theory)
  6. customare obtained in the form of an orange-coloured liquid (trans:cis ratio: 7.7:1)

Sources & evidence

ORD record
ord-d787b816d33b477dbe4c16c39852599e
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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