反応 #69176

反応方程式

NaOH

cyclopentylacetylene

n-butyllithium

phenyl cyanate

→

product

収率 95.0%

3-Cyclopentylprop-2-ynenitrile

収率 95.0%

溶媒

THF

hexane

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 5 minutes
2. 2
   抽出The product was extracted with diethyl ether
3. 3
   洗浄The extracts were washed with 6 N NaOH and with brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   その他decanted
6. 6
   その他the solvent was removed in vacuo

実験手順

To a solution of cyclopentylacetylene (0.50 g, 5.3 mmol) in THF (5 mL) at −78° C. was added 2.5 M n-butyllithium in hexane (2.23 mL). The mixture was stirred for 15 min followed by the dropwise addition of phenyl cyanate (0.70 g, 5.8 mmol) in THF (3 mL). The reaction was warmed to room temperature. Into the reaction mixture was poured 6 N NaOH, and the mixture was stirred for 5 minutes. The product was extracted with diethyl ether. The extracts were washed with 6 N NaOH and with brine, then dried over sodium sulfate, decanted and the solvent was removed in vacuo to afford product (600 mg, 95%). 1H NMR (300 MHz, CDCl3): δ □2.81-2.68 (m, 1H), 2.07-1.54 (m, 8H).

出典