反応 #53378

反応方程式

4-Iodoanisol

iodide

4-pentyn-1-ol

→

product 16

収率 88.9%

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

収率 88.9%

溶媒

diethylamine

反応条件

後処理

1. 1
   その他the solvent was removed under reduced pressure
2. 2
   workup.ADDITIONEthyl acetate (150 mL) was added to the residue
3. 3
   洗浄the mixture was washed with 2N HCl, brine and water
4. 4
   その他The organic fraction was isolated
5. 5
   乾燥dried with sodium sulfate
6. 6
   その他the solvent was removed under reduced pressure

実験手順

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).

出典