Ethyl isobutyrate → HCID 11482859, compound

Participants

Reaction Steps

A solution of lithium diisopropylamine in cyclohexane (0.15 mol, 100 ml) and tetrahydrofuran (150 ml) was cooled to -60° C. and treated with ethyl isobutyrate (18.59 g, 0.16 mole). The solution was stirred for 1 hour then treated with 1,6-dibromohexane (51.23 g, 0.21 mole), hexamethylphosphoramide (45 g) and was stirred at -70° C. for 1 hour. The solution was then warmed to room temperature and the solvent was removed under reduced pressure. The remaining solution was treated with saturated ammonium chloride solution (400 ml) and extracted with ethylacetate (2×200 ml). The ethyl acetate extracts were combined and washed with dilute hydrochloric acid (100 ml), sodium bicarbonate (100 ml) and then dried over magnesium sulphate. The solvent and unreacted starting material were removed by distillation to give the title compound as an oil.

Provenance & Evidence