反应详情

温度

70 °C

n-BuLi (2.2 M, 24.3 mL, 53.5 mmol) was added dropwise to a cooled (-78° C.) slurry of tetradecyne (10.3 g, 52.7 mmol) in anhydrous ether (60 mL) at a rate not allowing the temperature to rise above -40° C. The resulting slurry was stirred (5 minutes, 70° C.), then phenyl cyanate (6.9 g, 58.0 mmol) was added dropwise at a rate not allowing the temperature to rise above -60° C. The resulting slurry was stirred (45 minutes, -78° C.) then warmed (25° C.). The resulting solution was diluted with ether (140 mL), washed with 1.5 N NaOH (2×100 mL), washed with brine (1×100 mL), then dried (MgSO4), and concentrated in vacuo. The resulting oil was chromatographed on silica (pentane to 95:5 pentane:ether) to yield 9.0 g (77.8%) of 2-pentadecynenitrile as a pale yellow liquid.

1. customto rise above -40° C
2. customto rise above -60° C
3. stirringThe resulting slurry was stirred (45 minutes, -78° C.)
4. temperaturethen warmed (25° C.)
5. washwashed with 1.5 N NaOH (2×100 mL)
6. washwashed with brine (1×100 mL)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated in vacuo
9. customThe resulting oil was chromatographed on silica (pentane to 95:5 pentane:ether)