Ethyl isobutyrate → Ethyl 2,2-dimethylpent-4-ynoate

HRID 852389Notes

Reaction equation

HRID 852389 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.[C:9]([O:14][CH2:15][CH3:16])(=[O:13])C(C)C.[CH2:17](Br)[C:18]#[CH:19].OS([O-])(=O)=O.[K+]>C1COCC1>[CH2:15]([O:14][C:9](=[O:13])[C:6]([CH3:7])([CH3:8])[CH2:19][C:18]#[CH:17])[CH3:16]

Participants

6

Reactant 4

HCID 7342Ethyl isobutyrateHCID 7842Propargyl bromideHCID 516920Potassium bisulfateHCID 2724682Lithium diisopropylamide

Product 1

HCID 14459632Ethyl 2,2-dimethylpent-4-ynoateYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 22.0 ml (2.0 M in THF/n-heptane/ethylbenzene, 44 mmol) LDA in 40 ml THF was treated during 10 min at −78° C. with 5.47 ml (40 mmol) ethyl isobutyrate in 4.7 ml THF. After 1 h at this temperature, a solution of 4.90 ml (80% by weight in toluene, 44 mmol) of propargyl bromide in 7.5 ml THF was added dropwise. The solution was naturally warmed to 0° C. and after 2 h treated carefully with aqueous 10% KHSO4 and extracted with ether (three times). The organic phases were washed with aqueous 10% KHSO4 and aqueous 10% NaCl solution. The organic phase was dried (Na2SO4) and evaporated to give 5.70 g of the title compound as volatile orange liquid.

Workup

  1. extractionextracted with ether (three times)
  2. washThe organic phases were washed with aqueous 10% KHSO4 and aqueous 10% NaCl solution
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-d021079f259545bfb5834e92fe4c0b09
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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