Diphenylamine → HCID 57227171, compound

Participants

Reaction Steps

To a solution of 1.4 mL Me3Al (2.0M in hexanes) in 3.6 mL anhydrous CH2Cl2 under N2 was added 0.49 g of diphenylamine in one portion. After stirring 30 min, 0.35 g ethyl 4-(t-butyldimethylsilyloxy)-2-butynoate in 0.4 mL CH2Cl2 was added dropwise. The reaction was stirred overnight at room temperature, then heated in an oil bath at 35° overnight. The reaction was quenched by the addition of a few drops of 1N HCl, diluted with H2O, and extracted with CH2Cl2. The combined organics were with H2O and brine and dried over Na2SO4. Filtration, evaporation, and flash chromatography with a 10-15% Et2O/hexanes gradient provided 0.31 g of product.

Provenance & Evidence