Triethylamine → 2-(1-Dodecynyl)thiophene

Temperature

55 °C

To a solution of 2-iodothiophene (31.5 g), 1-dodecyne (2.5 g), triethylamine (105 ml), and tetrahydrofuran (100 ml) was added (bis)triphenylphosphine palladium(II)chloride (1.73 g) followed by copper(I)iodide (0.24 g). The reaction mixture was warmed to 55° C. and stirred for 7 hr. The solution was allowed to cool to room temperature and stirred overnight. The mixture was filtered, and the precipitate was washed with ethyl acetate. The filtrate was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with hexane). The appropriate fractions were collected and evaporated. The residue was distilled to afford 27.6 g (74%) of product, bp 145°-150° C. at 0.7 mm Hg.

1. temperatureto cool to room temperature
2. stirringstirred overnight
3. filtrationThe mixture was filtered
4. washthe precipitate was washed with ethyl acetate
5. additionThe filtrate was diluted with ethyl acetate
6. washwashed with water and brine
7. customThe organic phase was separated
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate was concentrated in vacuo
11. customchromatographed over silica gel (eluted with hexane)
12. customThe appropriate fractions were collected
13. customevaporated
14. distillationThe residue was distilled

ORD record

ord-a174aa9a1ba4428c8a0c98df6585a682

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05488063