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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence