Ethyl isobutyrate → Ethyl 2-dimethylstibanyl-2-methylpropionate

Participants

Reaction Conditions

Reaction Steps

A 3.48 g quantity (30 mmole) of ethyl isobutyrate was added to 50 ml of THF, and the mixture was chilled to −78° C. To the mixture was slowly added 16.5 ml (33 mmole) of lithium isopropylamide (product of Aldrich, 2.0M heptane-THF-ethylbenzene solution) over a period of 10 minutes. The reaction mixture was stirred while being held at −78° C. (for 1 hour). To the resulting solution was added 6.9 g (29.8 mmole) of dimethylstibanyl bromide at 0° C., followed by stirring at room temperature for 2 hours. After the completion of the reaction, the solvent was concentrated in a vacuum and subsequently distilled in a vacuum, giving 3.98 g of a colorless oily product (50.0% in yield), b.p. 53-55° C./1.6-1.8 mmHg. MS (HRMS), 1H-NMR and 13C-NMR revealed that the product was the desired one.

Provenance & Evidence