Tetrabutylammonium Fluoride → HCID 59153336, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium fluoride (TBAF) (23 mL, 1M in THF, 23 mmol) was added over 5 min to a solution of (E)-methyl 4-benzylidene-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (900 mg, 2.26 mmol) in cooled THF (0° C.). The reaction mixture was then heated for 4 h at 80° C. After 48 h at rt, the reaction mixture was partitioned between ether and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (cyclohexane/EtOAc:80/20) to afford the (E)-methyl 4-benzylidene-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (80 mg). LC/MS: 76%, m/z=267.

Provenance & Evidence