Potassium Phosphate, Tribasic → 2-(2,4,6-Trimethylphenyl)-3-methoxy-cyclopent-2-enone

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-bromo-3-methoxy-cyclopent-2-enone (32.3 g 169 mmol), 2,4,6-trimethylphenyl boronic acid (29.5 g, 180 mmol) and freshly ground potassium phosphate (63.7 g) in degassed toluene (800 ml) under N2 is added Pd(OAc)2 (896 mg, 8 mmol) and S-Phos (1.64 g, 4 mmol), and the reaction heated to 90° C. with stirring under N2 overnight. The reaction is partitioned between ethyl acetate (500 ml) and water (500 ml), and the organic layer is removed and the aqueous phase is extracted with ethyl acetate (2×300 ml). The combined organic extracts are evaporated under reduced pressure and the residue is purified to give 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (30.7 g).

Provenance & Evidence