Реакция #2808

Уравнение реакции

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

pyridine

2-(trimethylsilyl)ethanol

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid

→

title compound

Выход 81.0%

2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester

Выход 81.0%

Растворители

ethyl acetate

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураcool in an ice bath
2. 2
   workup.STIRRINGStir for 22 hours at 5° C.
3. 3
   workup.WAITat room temperature for 1.5 hours
4. 4
   workup.ADDITIONadd 0.6 times all reagents
5. 5
   workup.STIRRINGstir at room temperature overnight
6. 6
   Промывкаwash with 5% sulfuric acid (40 mL) and saturated sodium hydrogen carbonate (40 mL)
7. 7
   ЭкстракцияBack extract with methylene chloride (100 mL)
8. 8
   Промывкаwash with brine (30 mL)
9. 9
   Сушкаdry (Na2SO4)
10. 10
    ДругоеEvaporate the solvent in vacuo
11. 11
    Другоеpurify by silica gel chromatography (2:1 hexane/ethyl acetate)

Методика

Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid (2.47 g, 7.69 mmol) in tetrahydrofuran (35 mL) and cool in an ice bath. Treat with pyridine (1.6 mL, 20 mmol) and 2-(trimethylsilyl)ethanol (2.3 mL, 16 mmol). Stir for 30 minutes and add 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (2.21 g, 11.5 mmol). Stir for 22 hours at 5° C., then at room temperature for 1.5 hours. Cool to 0° C., add 0.6 times all reagents and stir at room temperature overnight. Dilute with ethyl acetate (150 mL), wash with 5% sulfuric acid (40 mL) and saturated sodium hydrogen carbonate (40 mL). Back extract with methylene chloride (100 mL), wash with brine (30 mL) and dry (Na2SO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give the title compound (2.61 g, 81%).

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