Water → Diethyl (2-methylbut-3-yn-2-yl)propanedioate

HRID 2049517Notes

Reaction equation

HRID 2049517 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].[CH3:13][C:14]([CH3:18])=[C:15]=[CH:16]Br.O>C(O)C>[CH3:13][C:14]([CH3:18])([C:15]#[CH:16])[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 110518111-Bromo-3-methylbuta-1,2-diene

Product 1

HCID 304028Diethyl (2-methylbut-3-yn-2-yl)propanedioate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl malonate (34.8 g.) was added to a solution of sodium (5.0 g.) in ethanol (500 ml.) and the mixture stirred for a few minutes. 3,3-Dimethyl-1-bromoallene (32.0 g.) was then added dropwise at the ambient temperature after which the mixture was refluxed for 3 hours. The ethanolic solution obtained was poured into an excess of water and the mixture extracted with chloroform (3×200 ml.). The extracts were combined, dried with anhydrous sodium sulphate and evaporated and the residual oil distilled under reduced pressure to yield ethyl 3,3-dimethyl-2-ethoxycarbonylpent-4-ynoate, as an oil b.p. 56°-60°/0.1 mm.Hg.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe ethanolic solution obtained
  3. extractionthe mixture extracted with chloroform (3×200 ml.)
  4. dry with materialdried with anhydrous sodium sulphate
  5. customevaporated
  6. distillationthe residual oil distilled under reduced pressure

Sources & evidence

ORD record
ord-c22eabe190fd46208fa4ef8b54826fbe
Source dataset
uspto-grants-1980_04
Patent number
US04198347

Reaction notes

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