Tributyl(prop-1-yn-1-yl)stannane → Rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone (1.0 g, 2.5 mmol) in toluene (10 ml) is added tributyl(1-propynyl)tin (1.55 ml, 5.18 mmol) and tetrakistriphenylphosphine palladium(0) (0.5 g, 0.5 mmol) under a nitrogen atmosphere. The reaction mixture is heated at 130°C. for 40 minutes under microwave irradiation, then diluted with distilled water (20 ml) and extracted with ethyl acetate (50 ml×2). The combined organic fractions are washed with distilled water, brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo to afford rac-2-(2,6-dimethyl-4-prop-1-ynylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone. This material is used directly in the next step without further purification.

Provenance & Evidence