反応 #317513

反応方程式

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

収率 5.9%

溶媒

ethyl acetate

DMF

反応条件

後処理

1. 1
   温度After cooling the reaction solution to room temperature
2. 2
   洗浄the solution was washed 3 times with water
3. 3
   乾燥by drying the organic layers over anhydrous sodium sulfate
4. 4
   その他After removing anhydrous sodium sulfate
5. 5
   ろ過by filtration
6. 6
   濃縮the filtrate was concentrated
7. 7
   その他The residue was purified by column chromatography (silica gel, eluent: cyclohexane/chloroform=2/1→1/4)

実験手順

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).

出典