반응 #317513

반응 방정식

tris(2-methylphenyl)phosphine

2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester

tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol

potassium carbonate

→

(E)-2-(2,6-dichlorobenzamido)-5-[4-(4-hydroxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester

수율 5.9%

용매

ethyl acetate

DMF

반응 조건

후처리

1. 1
   온도After cooling the reaction solution to room temperature
2. 2
   세척the solution was washed 3 times with water
3. 3
   건조by drying the organic layers over anhydrous sodium sulfate
4. 4
   기타After removing anhydrous sodium sulfate
5. 5
   여과by filtration
6. 6
   농축the filtrate was concentrated
7. 7
   기타The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/4)

실험 절차

Under an argon atmosphere, palladium acetate (4.7 mg) and tris(2-methylphenyl)phosphine (6.1 mg) were added to a suspension of 2-(2,6-dichlorobenzamido)pent-4-enoic acid methyl ester (60.4 mg), tetrahydro-4-(4-iodophenyl)-2H-pyran-4-ol (60.8 mg) and potassium carbonate (41.5 mg) in DMF (4 ml), and the resulting mixture was stirred at 80° C. for 6 hours. After cooling the reaction solution to room temperature, ethyl acetate was added thereto and the solution was washed 3 times with water and once with saturated brine, followed by drying the organic layers over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/4) and thereafter by thin layer chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate=1/1) to obtain (E)-2-(2,6-dichlorobenzamido)-5-[4-(4-hydroxytetrahydropyran-4-yl)-phenyl]pent-4-enoic acid methyl ester (5.6 mg).

출처