Water → Benzene, 1-ethynyl-3-nitro-

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(3-nitrophenyl)-2-trimethylsilylacetylene (43 g, 0.197 mol) in diethylether (800 mL) is cooled to 0° C. under argon atmosphere. To this solution is added, dropwise over 30 min, a solution of TBAF (1M in THF, 217 mL, 0.217 mol) maintaining temperature below 10° C. The reaction mixture is stirred for 30 min at 0° C. The reaction mixture is poured into water and extracted with diethyl ether (×2). The organic layers are combined, washed with brine, and dried (Na2SO4). The solvents are removed under reduced pressure. The residue is purified by silica-gel chromatography with Hexane/EtOAc=20/1 to give orange oil (26 g).

Provenance & Evidence