تفاعل #2808

معادلة التفاعل

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

المردود 81.0%

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

المردود 81.0%

المذيبات

ethyl acetate

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcool 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
   غسيلwash with 5% sulfuric acid (40 mL) and saturated sodium hydrogen carbonate (40 mL)
7. 7
   استخلاصBack extract with methylene chloride (100 mL)
8. 8
   غسيلwash with brine (30 mL)
9. 9
   تجفيفdry (Na2SO4)
10. 10
    أخرىEvaporate the solvent in vacuo
11. 11
    أخرىpurify by silica gel chromatography (2:1 hexane/ethyl acetate)

الإجراء التجريبي

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%).

المصدر