Ethyl Acrylate → 3-[3-(1-Amino-1-methyl-ethyl)-phenyl]-2-methylacrylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

The mixture of 1-(3-bromo-phenyl)-1-methyl-ethylamine (0.74 g, 3.5 mmol), tris(dibenzylideneacetone)dipalladium (0.19 g, 0.21 mmol), and N-methyldicyclohexylamine (10 mmol) was purged with nitrogen followed by the addition of 1,4-dioxane (7 mL) and tri-tert-butylphospine (85 mg, 0.42 mmol). The mixture was again purged with nitrogen and ethyl acrylate (0.75 mL, 7.0 mmol) was added. The mixture was heated to 80° C. for 1 h, brought to room temperature, poured into water (50 mL) and extracted with ethyl acetate (100 mL). The organic layer was separated, washed again with water, dried over magnesium sulfate, concentrated and chromatographed on silica gel using 0-4% MeOHI/CH2Cl2 to afford yellow oil.

Provenance & Evidence