Sodium hydride → HCID 58453198, compound

HRID 2109525Notes

Reaction equation

HRID 2109525 reaction equation
[H-].[Na+].CS(O[CH:8]([CH:20]1[CH2:22][CH2:21]1)[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18])(=O)=O>CS(C)=O>[N+:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH:10]1[CH2:9][CH:8]1[CH:20]1[CH2:22][CH2:21]1)([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 866212421-Cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate

Product 1

HCID 58453198HCID 58453198, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

0.48 g of sodium hydride (12 mmol) is introduced into 10 ml of dimethyl sulfoxide and a solution consisting of the 1-cyclopropyl-3-(2-nitrophenyl)-propyl methanesulfonate and 15 ml of DMSO is added. Stirring is then 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 (64% of theory) is obtained in the form of a brownish liquid (trans:cis ratio: 4.1:1).

Workup

  1. additionis added
  2. extractionExtraction
  3. dry with materialthe organic phase is dried over sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customto remove by-products (eluant: ethyl acetate/hexane 1:15)
  6. customAfter removal of the eluant

Sources & evidence

ORD record
ord-800197e7fa8b4143b92f742ae23d7109
Source dataset
uspto-grants-2009_04
Patent number
US07514584B2

Reaction notes

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