Ethyl cyanoacetate → Ethyl 1-cyanocyclopentane-1-carboxylate

HRID 2242380Notes

Reaction equation

HRID 2242380 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].Br[CH2:10][CH2:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:7]([O:6][C:4]([C:3]1([C:1]#[N:2])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:5])[CH3:8]

Participants

6

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 80561,4-DibromobutaneHCID 10796Cesium carbonate

Product 1

HCID 15688760Ethyl 1-cyanocyclopentane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl cyanoacetate (2.50 g, 22 mmol) and 1,4-dibromobutane (5.00 g, 23.0 mmol) were dissolved in anhydrous DMF (20 ml) under nitrogen and cesium carbonate (21.0 g, 64 mmoles) added with water bath cooling. After stirring at room temperature for 18 h the reaction was diluted with water and extracted with ethyl acetate (2×80 ml), the organic layers were combined and washed with water (40 ml) and saturated aqueous sodium chloride solution (25 ml). The organics were dried over magnesium sulphate, filtered and evaporated under reduced pressure to give 1-cyano-cyclopentanecarboxylic acid ethyl ester as an almost colourless oil (3.64 g, 98%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate (2×80 ml)
  3. washwashed with water (40 ml) and saturated aqueous sodium chloride solution (25 ml)
  4. dry with materialThe organics were dried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a118824d6a1f4dd0b79e9592db6bbda0
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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