반응 #528132

반응 방정식

1-iodonaphthalene

4-pentyn-1-ol

4-pentyn-1-ol

→

5-(naphth-1-yl)-4-pentyn-1-ol

수율 68.7%

용매

diethylamine

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of addition
2. 2
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for about 18 hours
3. 3
   workup.STIRRINGthe reaction mixture was stirred for an additional six hours
4. 4
   세척Elution
5. 5
   농축The eluate was concentrated under reduced pressure

실험 절차

Under a nitrogen atmosphere, a mixture of 4.0 mL (0.027 mole) of 1-iodonaphthalene, 0.1 gram (0.0003 mole) of copper(I) iodide, and 0.19 gram (0.0003 mole) of bis(triphenylphosphine)palladium(II) chloride in 75 mL of diethylamine was stirred, and 2.6 mL (0.027 mole) of 4-pentyn-1-ol was added in one portion. Upon completion of addition, the reaction mixture was stirred at ambient temperature for about 18 hours. Gas chromatographic (GC) analysis of the reaction mixture indicated that the reaction had not gone to completion. An additional 0.5 mL of the 4-pentyn-1-ol was added, and the reaction mixture was stirred for an additional six hours. GC analysis of the reaction mixture indicated that the reaction was complete. The reaction mixture was passed through a column of silica gel. Elution was accomplished using methylene chloride. The eluate was concentrated under reduced pressure, yielding 3.9 grams of 5-(naphth-1-yl)-4-pentyn-1-ol. The NMR spectrum was consistent with the proposed structure.

출처