Acetic Acid → Methyl 2-cyano-4-methylpent-2-enoate

HRID 1297231Notes

Reaction equation

HRID 1297231 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].[C:6]([CH2:8][C:9]([O:11][CH3:12])=[O:10])#[N:7].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1C=CC=CC=1>[CH3:12][O:11][C:9](=[O:10])[C:8]([C:6]#[N:7])=[CH:1][CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 7747Methyl cyanoacetateHCID 517165Ammonium Acetate

Product 1

HCID 53793275Methyl 2-cyano-4-methylpent-2-enoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of isobutyraldehyde (18.2 mL, 200 mmol) in dry benzene (20 mL) was added methyl cyanoacetate (18 mL, 200 mmol), ammonium acetate (2 g) and glacial acetic acid (4 mL). The reaction mixture was' stirred at 60° C. for 30 minutes and allowed to cool to room temperature. Excess of solvents was removed in vacuo and the residue was dissolved in EtOAc (200 mL). The organic layer was washed with water, dried over sodium sulfate and evaporated to give 2-cyano-4-methyl-pent-2-enoic acid methyl ester as pale yellow oil. Further purification of the pale yellow oil by distillation (7 mm Hg) gave product 2 (27.4 g, 56%) as colorless oil: 1H NMR (300 MHz, CDCl3) δ 1.16 (d, J=6.6 Hz, 6H), 2.96-3.04 (m, 1H), 3.87 (s, 3H), 7.47 (d, J=10.5 Hz, 1H).

Workup

  1. temperatureto cool to room temperature
  2. customExcess of solvents was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-df4e111da33945948d792734eb28e3c6
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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