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

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of THF (100 ml) is added a 1.5M solution of LDA in cyclohexane (260 mL, 390 mmol) via cannulation, followed by the addition of ethyl isobutyrate. The mixture is allowed to stir at −78° C. for 1 hr then propargyl bromide is added dropwise. The reaction mixture is allowed to warm to 23° C. then stirred overnight. The mixture is then treated with saturated aqueous NH4Cl, extracted with EtOAc, dried over magnesium sulfate, filtered, then concentrated in vacuo to give the title intermediate (54.7 g, 95%).

Provenance & Evidence