Hydrochloric Acid → HCID 14985749, compound

Participants

Reaction Steps

478 mg (3 mmol) of methyl N,N-diisopropylcarbamate are lithiated with 392 mg (3.3 mmol) of TMEDA in 4 ml of THF at -78° C. using 3.3 mmol of sec-BuLi. After 1 h, the reaction mixture is treated with 144 mg (2 mmol) of isobutyraldehyde and stirred for 21 h. The reaction mixture is then treated at -78° C. with 10 ml of 2N hydrochloric acid and 10 ml of ether and the mixture is warmed to room temperature. The phases are separated, the aqueous phase is extracted twice with ether and the combined organic phases are neutralized with saturated NaHCO3 solution. After drying over magnesium sulphate, the solvent is stripped off and the crude product of 500 mg weight is purified by chromatography on silica gel using ether/petroleum ether (1:3). 299 mg (64.6% of theory) of the title compound are obtained as a colorless liquid.

Provenance & Evidence