Ethyl cyanoacetate → Ethyl 1-cyanocyclohexane-1-carboxylate

HRID 2366738Notes

Reaction equation

HRID 2366738 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]Br.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][C:19]#[N:20])[CH3:15]>CN(C=O)C>[C:19]([C:18]1([C:17]([O:16][CH2:14][CH3:15])=[O:21])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)#[N:20]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 81001,5-DibromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 10997650Ethyl 1-cyanocyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (30.4 g, 0.220 mol) and 1,5-dibromopentane (13.6 mL, 0.100 mol) were sequentially added to a solution of ethylcyanoacetate (10.6 mL, 0.100 mol) in DMF (100 mL), and the reaction was stirred overnight at ambient temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic fraction was separated, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide ethyl 1-cyanocyclohexanecarboxylate.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customthe organic fraction was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-58ff80168bd64c3785710494ccb51177
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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