Reaction #4613

Reaction equation

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

Yield 96.5%

Solvents

—

ice water

dichloromethane

dichloromethane

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   Washby washing with water, saturated aqueous solution of sodium hydrogen carbonate in the order
2. 2
   DryingThe organic layer is dried (magnesium sulfate)
3. 3
   Concentrationconcentrated to about 20 ml at a temperature not
4. 4
   Otherexceeding 30° C
5. 5
   DryingThe 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
   Extractionwhich is subjected to extraction with ethyl acetate
9. 9
   Washwashed with water
10. 10
    Dryingdried (magnesium sulfate)
11. 11
    Otherby removing the solvent
12. 12
    Otherby evaporation under reduced pressure

Procedure

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%).

Source