Diisopropylamine → Di-tert-butyl 3-hydroxy-3-methylpentanedioate

Participants

Reaction Conditions

Reaction Steps

187 g of a solution of 19.5% butyllithium in cyclohexane (36.4 g of butyllithium) were added over 5 minutes at -40° C. under argon to 500 ml of tetrahydrofuran and then 57.5 g of diisopropylamine were added over 5 minutes at -40° C. The mixture was stirred at -40° C. for 30 minutes and 66 g of tert.-butyl acetate were added thereto at -40° C. The mixture was stirred at -40° C. for 30 minutes and then 27.5 g (≃0.55 mole per mole of tert.-butyl acetate) of ethyl acetate were added at -40° C. over 30 minutes. The mixture was stirred at -40° C. for two hours and the temperature allowed to rise to 20° C. under reduced pressure. The mixture was evaporated to dryness under reduced pressure at 20° C. and the residue was taken up in 200 ml of methylene chloride. The solution was cooled to 0° C. and 100 ml of water were added. The decanted aqueous phase was extracted with methylene chloride and the combined organic phases were adjusted to a pH of 1 by addition of 22° Be hydrochloric acid. The organic phase was washed with water, dried and evaporated to dryness under reduced pressure to obtain a lightly colored liquid which was rectified at 1 mm Hg to obtain 25 g of ditert.-butyl 3-methyl-3-hydroxy-glutarate with a boiling point of 95°±` C. at1 mm Hg.

Provenance & Evidence