Potassium tert-butoxide → HCID 58453198, compound

HRID 2109527Notes

Reaction equation

HRID 2109527 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+]>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 23665647Potassium tert-butoxideHCID 866212421-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

Product 1

HCID 58453198HCID 58453198, compoundYield 65%

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 0.28 g of potassium tert-butanolate (2.48 mmol) is added, and stirring is carried out for 3 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, 0.3 g of 2-(2-nitrophenyl)-bicyclopropane (65% of theory) is obtained in the form of a brownish liquid (trans:cis ratio: 4.7:1).

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 1:15)
  5. customAfter removal of the eluant

Sources & evidence

ORD record
ord-1c532c38b96a47baae4a443e463ff098
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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