Cerium(III) chloride → HCID 54032203, compound

Participants

Reaction Steps

To anhydrous cerium chloride (3.16 g, 12.8 mmol) dry tetrahydrofuran (50 mL) was added with stirring under argon and stirring was continued for 2 hours at room temperature. The resultant suspension was then cooled to -78° C., and 6.4 mL of n-butyllithium (2.0M in pentane) was added with stirring, whereupon the color of the suspension turned from white to yellow. After maintaining the same temperature for 30 minutes, (2,6-dimethyl-4-methoxyphenyl)-(3-isopropyl-4-methoxyphenyl) methanone (10) (1 g, 3.20 mmol) in tetrahydrofuran (5 mL) was added and the mixture was stirred for 3 hours at -78° C. and for 2 hours at 0° C. The reaction mixture was treated with sat. NH4Cl solution, filtered through Celite, and extracted with ethyl acetate. The combined extracts were dried (Na2SO4), evaporated, and the residue was purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate) to give (2,6-dimethyl-4-methoxyphenyl)-(6-n-butyl-3-isopropyl-4-methoxyphenyl) methanone (15) (500 mg, 43%); 1HNMR (CDCl3) δ 0.98 (t, 3H), 1.03 (d, 6H), 1.41 (m, 2H), 1.59 (m, 2H), 2.09 (s, 6H), 3.05 (t, 2H), 3.14 (heptet, 1H),3.86 (d, 6H), 6.52 (d, 2H), 6.73 (s, 2H), 7.22 (s, 1H).

Provenance & Evidence