Water → Ethyl 2-cyano-3,3-dimethylpent-4-ynoate

HRID 2049518Notes

Reaction equation

HRID 2049518 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[Na].Br[CH:11]=[C:12]=[C:13]([CH3:15])[CH3:14].O>C(O)C>[C:1]([CH:3]([C:13]([CH3:15])([CH3:14])[C:12]#[CH:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7764Ethyl cyanoacetateHCID 5360545SodiumHCID 110518111-Bromo-3-methylbuta-1,2-diene

Product 1

HCID 14985551Ethyl 2-cyano-3,3-dimethylpent-4-ynoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl cyanoacetate (77.0 g.) was slowly added at 40° C. to a stirred solution of sodium (15.7 g.) in ethanol (400 ml.) and 15 minutes after the addition was completed 1-bromo-3,3-dimethylallene (100 g.) was carefully added over about 30 minutes. The mixture was then heated at the reflux temperature for a period of 2.5 hours and then kept at the ambient temperature for a further 20 hours. The mixture was then poured into an excess of water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulphate and concentrated by evaporation of the solvent. The residual oil was distilled and ethyl 2-cyano-3,3-dimethylpent-4-ynoate was obtained as a colourless oil (boiling point 75°-76° C./0.1 mm Hg.).

Workup

  1. additionafter the addition
  2. additionwas carefully added over about 30 minutes
  3. temperatureThe mixture was then heated at the reflux temperature for a period of 2.5 hours
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. concentrationconcentrated by evaporation of the solvent
  8. distillationThe residual oil was distilled

Sources & evidence

ORD record
ord-a2e749ab31874b2a88bb2bdea6704eb0
Source dataset
uspto-grants-1980_04
Patent number
US04198347

Reaction notes

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