Ethyl trifluoroacetate → Lithium diisopropylamide

Participants

Reaction Conditions

Reaction Steps

A solution of LDA (95.4 mmol) in THF was prepared at −10° C. and cooled to −78° C. To the LDA was added a solution of 2-mercaptothiazole (10.00 g, 85.3 mmol) in 25 mL of THF. After 15-30 min of stirring, ethyl trifluoroacetate (13.2 mL, 110.9 mmol) in 15 mL of THF was added. The solution was brought to −10° C. and quenched with NH4Cl followed by HCl (10%) and diluted with EtOAc. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over anhydrous MgSO4. The solvent was evaporated and the residue chromatographed on silica gel (toluene/acetone; 8:2 with 1% methanol) to give the title compound.

Provenance & Evidence