反応 #81487

反応方程式

2-acetyl-6-bromopyridine

propargyl alcohol

→

2-acetyl-6-(3-hydroxy-2-propynyl)pyridine

収率 50.0%

溶媒

triethylamine

water

反応条件

後処理

1. 1
   抽出extracted with ether
2. 2
   洗浄the organic layer was washed with water (2x), brine
3. 3
   乾燥dried over magnesium sulfate
4. 4
   濃縮The organic solution was concentrated in vacuo
5. 5
   その他the residue was purified by MPLC (silica gel 60, hexane/ethyl acetate, 1:1)

実験手順

A suspension of 3 g (15.1 mmol) of 2-acetyl-6-bromopyridine, 0.89 g (15.9 mmol) of propargyl alcohol, 0.078 g of CuI, 300 mg of PdCl2 (P(Ph)3)2 in 60 ml of triethylamine was stirred under nitrogen at room temperature for 6 h. The mixture was diluted with water, extracted with ether, and the organic layer was washed with water (2x), brine, and dried over magnesium sulfate. The organic solution was concentrated in vacuo and the residue was purified by MPLC (silica gel 60, hexane/ethyl acetate, 1:1) to afford 1.3 g (50%) of 2-acetyl-6-(3-hydroxy-2-propynyl)pyridine, as a solid product.

出典