تفاعل #5679

معادلة التفاعل

sodium hydride

ethyl diethylphosphonoacetate

5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

→

5-ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling
2. 2
   workup.STIRRINGthe mixture is further stirred under ice-
3. 3
   درجة الحرارةcooling for 10 minutes
4. 4
   workup.STIRRINGthe mixture is stirred at room temperature for 6 hours
5. 5
   استخلاصextracted with ethyl acetate (300 ml)
6. 6
   غسيلThe extract is washed with brine (300 ml)
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent is distilled off
9. 9
   أخرىThe resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate: n-hexane=1:2)

الإجراء التجريبي

To tetrahydrofuran (200 ml) is added sodium hydride (60%, 0.85 g), and thereto is added dropwise ethyl diethylphosphonoacetate (4.68 ml) with stirring under ice-cooling, and the mixture is further stirred under ice-cooling for 10 minutes. To the reaction mixture is added 5-oxo-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.10 g), and the mixture is stirred at room temperature for 6 hours. The reaction solution is poured into ice-water (200 ml), and extracted with ethyl acetate (300 ml). The extract is washed with brine (300 ml), dried over magnesium sulfate, and the solvent is distilled off. The resulting residue is purified by silica gel column chromatography (eluent; ethyl acetate: n-hexane=1:2) to give 5-ethoxycarbonylmethylidene-7-chloro-1-[2-methyl-4-(2-methylbenzoylamino)benzoyl]-2,3,4,5-tetrahydro-1H-benzazepine (2.22 g) in the form of a mixture of the E-type compound and the Z-type compound thereof, as colorless amorphous.

المصدر