Tetrabutylammonium Fluoride → Tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (10.1 g, 29.4 mmol) in anhydrous tetrahydrofuran (150 ml) was added at 0° C. tetra-n-butylammonium fluoride (1M tetrahydrofuran solution, 29.4 ml, 29.4 mmol). After stirring at 0° C. for 45 mins, the mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate, and the extract was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate (7.7 g, yield 96%) as a yellow solid.

Provenance & Evidence