Ethyl acetate hexane → 4-Methyl-2-(2-methylprop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester

Participants

Reaction Steps

5.6 ml (2.8 mmol, 2M in THF) (2-methylprop-1-enyl)magnesium bromide was added in drops at 0° C. to a solution of 600 mg (1.4 mmol) 4-methyl-7-(trifluoromethyl)-2-(trifluoromethylsulfonyl-oxy)quinoline-3-carboxylic acid ethyl ester and 75 mg (0.1 mmol) Ni(dppp)Cl2 in THF (10 ml). The mixture was subsequently stirred for 16 h at RT and thereafter quenched at 0° C. with a sat. aq. NH4Cl sol. It was then extracted with EtOAc and the organic phase was washed with water and brine, dried over Na2SO4 and concentrated in a vacuum. After CC (EtOAc/hexane 1:19) of the residue, 200 mg (0.6 mmol, 43%) 4-methyl-2-(2-methylprop-1-enyl)-7-(trifluoromethyl)quinoline-3-carboxylic acid ethyl ester was obtained.

Provenance & Evidence