Methyl cyanoacetate → methyl 1-cyanocyclopropanecarboxylate

HRID 1991231Notes

Reaction equation

HRID 1991231 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16]Br>CN(C)C=O>[C:1]([C:3]1([C:4]([O:6][CH3:7])=[O:5])[CH2:16][CH2:15]1)#[N:2]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 353030methyl 1-cyanocyclopropanecarboxylateYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl cyanoacetate (21.6 ml, 244.0 mmol) and potassium carbonate (52.9 g, 383.0 mmol) in N,N-dimethylformamide (200 ml) was added 1,2-dibromoethane (15.0 ml, 174.0 mmol). The reaction mixture was stirred at room temperature for 16 h and then filtered. The filtrate was partitioned between diethyl ether and brine and the organic phase was separated, washed with brine, dried (MgSO4) and concentrated in vacuo to give the title compound (15.1 g).

Workup

  1. filtrationfiltered
  2. customThe filtrate was partitioned between diethyl ether and brine
  3. customthe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb744d14a6324233a5148e7b0f260805
Source dataset
uspto-grants-2010_01
Patent number
US07645786B2

Reaction notes

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