Diisopropylamine → HCID 68829402, compound

Participants

Reaction Conditions

Reaction Steps

To a dry round bottom flask was added 3.5 mL of diisopropylamine and 20 mL THF under N2. The solution was cooled to −78° C. and stirred. A solution of n-BuLi (15 mL, 1.6 mL) was added and the reaction mixture was stirred for an additional 20 min. EtOAc (2.0 mL in 10 mL THF) was added slowly at −78° C. and the resulting solution was stirred for 20 min. 2-Benzyl-4-methoxy-1-(2-nitrovinyl)benzene (5.46 g, 19.1 mmol) was added (in 30 mL THF) and stirred for 2 h. The mixture was slowly warmed up to r.t. and quenched with sat. NH4Cl solution. The mixture was extracted with EtOAc (2×100 mL), washed with water and brine, and then dried. After removal of the solvent, the residue was purified on silica gel to give 5.3 g of the desired product. Yield: 74%.

Provenance & Evidence