반응 #168521

반응 방정식

4-iodobenzonitrile

triethylamine

But-3-ynylcarbamic acid tert-butyl ester

→

product 56

수율 99.0%

[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester

수율 99.0%

용매

THF

반응 조건

후처리

1. 1
   온도cooled
2. 2
   기타argon purged
3. 3
   workup.STIRRINGAfter stirring for 10 min
4. 4
   기타the ice bath was removed
5. 5
   workup.STIRRINGto stir for an additional 2 h
6. 6
   기타After evaporating the solvent
7. 7
   기타the crude product was chromatographed with methylene chloride/ethyl acetate (20:1) as eluant
8. 8
   기타Evaporation of the solvent

실험 절차

But-3-ynylcarbamic acid tert-butyl ester (3.66 g, 22 mmol) was added dropwise to an ice cooled, stirring, argon purged mixture of 4-iodobenzonitrile (4.5 g, 19.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.69 g, 0.98 mmol), copper (1) iodide (0.19 g, 0.98 mmol), triethylamine (11 mL, 78.4 mmol), and THF (24 mL). After stirring for 10 min, the ice bath was removed, and the reaction was allowed to stir for an additional 2 h. The reaction mixture was passed through a pad of silica gel with methylene chloride/ethyl acetate (5:1) as eluant. After evaporating the solvent, the crude product was chromatographed with methylene chloride/ethyl acetate (20:1) as eluant. Evaporation of the solvent, followed by placement under vacuum for 1 h, afforded the pure product 56 (5.2 g, 99%) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.46 (s, 9H), 2.64 (t, 2H), 3.37 (m, 2H), 4.85 (br s, 1H), 7.47 (d, 2H), 7.58 (d, 2H).

출처