反应详情

温度

55 °C

A mixture of 3-bromobenzaldehyde (51.8 g), 1-undecyne (48.6 g), bis(triphenylphosphine)palladium(II)chloride (3.37 g), copper iodide (457 mg), and triethylamine (196 ml) in dry tetrahydrofuran (300 ml) was stirred for 4 hrs at 55° C. The reaction mixture was filtered, the filtrate was diluted with ethyl acetate, and the solution was washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was chromatographed on 300 g of silica gel (1:4-ethyl acetate:hexane). The appropriate fractions were collected and evaporated. Distillation of a 40-g sample of the residue (81.3 g) gave 9.5 g (13%) of the product, bp 172°-174° C. (0.5 mm mercury).

1. filtrationThe reaction mixture was filtered
2. additionthe filtrate was diluted with ethyl acetate
3. washthe solution was washed with water and brine
4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was concentrated in vacuo
7. customThe residue was chromatographed on 300 g of silica gel (1:4-ethyl acetate:hexane)
8. customThe appropriate fractions were collected
9. customevaporated
10. distillationDistillation of a 40-g sample of the residue (81.3 g)