Potassium Hydroxide → HCID 58453198, compound

HRID 2109521Notes

Reaction equation

HRID 2109521 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.[OH-].[K+]>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

4

Reactant 2

HCID 14797Potassium HydroxideHCID 866212421-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

Product 1

HCID 58453198HCID 58453198, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 1-cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate is dissolved in 15 ml of dimethyl sulfoxide and 0.17 g of potassium hydroxide (2.48 mmol) is added, and stirring is carried out for 5 hours at ambient temperature. The reaction mixture is added to ice-water. 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 1:15). After removal of the eluant, 0.28 g of 2-(2-nitrophenyl)-bicyclopropane (61% of theory) is obtained in the form of a brownish liquid (trans:cis ratio: 4.5:1). 1H-NMR of trans-2-(2-nitrophenyl)-bicyclopropane (CDCl3-ppm): 0.17/m/1H, 0.19/m/1H, 0.42/m/1H, 0.48/m/1H, 0.83/m/1H, 0.84/m/1H, 0.99/m/1H, 1.13/m/1H, 2.17/m/1H, 7.10/dd/1H, 7.25/m/1H, 7.45/m/1H, 7.78/dd/1H); 1H-NMR of cis-2-(2-nitrophenyl)-bicyclopropane (CDCl3-ppm): −0.09/m/1H, 0.02/m/1H, 0.06/m/1H, 0.27/m/1H, 0.71/m/1H, 0.85/m/1H, 0.98/m/1H, 1.10/m/1H, 2.53/m/1H, 7.35/m/1H, 7.45/m/1H, 7.52/m/1H, 7.92/dd/1H.

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 1:15)
  5. customAfter removal of the eluant

Sources & evidence

ORD record
ord-25fa25a212084e70b75f7e78c8609016
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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