반응 #53378

반응 방정식

4-Iodoanisol

iodide

4-pentyn-1-ol

→

product 16

수율 88.9%

5-(4-Methoxyphenyl)pent-4-yn-1-ol

수율 88.9%

용매

diethylamine

반응 조건

후처리

1. 1
   기타the solvent was removed under reduced pressure
2. 2
   workup.ADDITIONEthyl acetate (150 mL) was added to the residue
3. 3
   세척the mixture was washed with 2N HCl, brine and water
4. 4
   기타The organic fraction was isolated
5. 5
   건조dried with sodium sulfate
6. 6
   기타the solvent was removed under reduced pressure

실험 절차

4-Iodoanisol (10 g, 42 mmol), palladium (II) chloride (0.2 g, 1.1 mmol) and triphenylphosphine (0.6 g, 2.2 mmol) were dissolved in diethylamine (100 mL) then cupper(I) iodide (0.5 g, 2.2 mmol) and 4-pentyn-1-ol (5 mL, 53 mmol) were added. The reaction mixture was stirred overnight at room temperature, then the solvent was removed under reduced pressure. Ethyl acetate (150 mL) was added to the residue and the mixture was washed with 2N HCl, brine and water. The organic fraction was isolated, dried with sodium sulfate and the solvent was removed under reduced pressure. The product 16 (7.1 g. 87%) was isolated by flash chromatography (silica gel, 1:2 ethyl acetate/hexanes) as an oily yellow solid. 1H NMR (300 MHz, CDCl3) δ1.88 (m, 2H), 2.53 (m, 2H), 3.72 (s, 3H), 3.74 (m, 2H), 6.83 (d, 2H), 7.45 (d, 2H).

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