Potassium tert-butoxide

Description

Potassium t-butoxide (t-BuOK) is a strong, non-nucleophilic base. The pKa of its conjugate acid is about 17. Similar bases include sodium t-butoxide (t-BuONa) and lithium t-butoxide (t-BuOLi).

The Uses of Potassium tert-butoxide

To a suspension of methyl triphenylphosphonium bromide (2.4 g, 6.6 mmol) in THF was added tBuOK (1M in THF, 7.1 mmol) at RT. After stirring for 90 min, a solution of the SM (1.25 g, 3.35 mmol) in dry THF was added. The resulting mixture was stirred at RT for 18 h, after which time it was partitioned between saturated NH4Cl and MTBE. The org layer was dried (Na2SO4), concentrated, and purified by flash chromatography (25-30% EtOAc/hexane) to provide the product as a colorless oil. [0.3 g, 24%] [UK Pat App GB2463151A, page 141]

The Uses of Potassium tert-butoxide

Potassium tert-Butoxide is used in the synthesis of many organic compounds primarily as a strong base. In particular, it is used as a reagent in the base- catalyzed carbonylation of amines for the synthesis of N-Formamides.