反応 #4613

反応方程式

Phosphorus pentachloride

sodium hydride

methyl metahydroxybenzoate

1-phenyl-1-(3-pyridyl)-2-propen-1-ol

→

methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate

収率 96.5%

溶媒

—

ice water

dichloromethane

dichloromethane

dimethylformamide

dimethylformamide

反応条件

後処理

1. 1
   洗浄by washing with water, saturated aqueous solution of sodium hydrogen carbonate in the order
2. 2
   乾燥The organic layer is dried (magnesium sulfate)
3. 3
   濃縮concentrated to about 20 ml at a temperature not
4. 4
   その他exceeding 30° C
5. 5
   乾燥The solution was further dried with molecular sieves 4A
6. 6
   workup.STIRRINGThe mixture was stirred for 30 minutes at 0° C., to which
7. 7
   workup.STIRRINGby stirring at room temperature for 1.5 hours
8. 8
   抽出which is subjected to extraction with ethyl acetate
9. 9
   洗浄washed with water
10. 10
    乾燥dried (magnesium sulfate)
11. 11
    その他by removing the solvent
12. 12
    その他by evaporation under reduced pressure

実験手順

Phosphorus pentachloride (3.0 g, 14.2 mmoles) was suspended in dichloromethane (4 ml). To the suspension was added dropwise a solution of 1-phenyl-1-(3-pyridyl)-2-propen-1-ol (2.0 g, 9.5 mmoles) in dichloromethane (20 ml) at 0° C., then the mixture was stirred for one hour at room temperature, followed by washing with water, saturated aqueous solution of sodium hydrogen carbonate in the order. The organic layer is dried (magnesium sulfate), and concentrated to about 20 ml at a temperature not exceeding 30° C. The solution was further dried with molecular sieves 4A. This solution was named as (a) solution. Separately, sodium hydride (400 mg, 10 mmoles) is suspended in dimethylformamide (5 ml). To the suspension was added dropwise methyl metahydroxybenzoate (1.37 g, 9.0 mmoles) dissolved in dimethylformamide (5 ml). The mixture was stirred for 30 minutes at 0° C., to which was added dropwise the (a) solution, followed by stirring at room temperature for 1.5 hours. The reaction mixture was poured in ice-water, which is subjected to extraction with ethyl acetate, washed with water and dried (magnesium sulfate), followed by removing the solvent by evaporation under reduced pressure. The residue was subjected to silica-gel column chromatography, using ether-ethyl acetate (7:3) as eluant to yield methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate (If-56) (3.0 g, 92%).

出典