تفاعل #215508

معادلة التفاعل

hydrochloric acid

sodium hydride

methylphenylsulfone

tetrahydrofuran

methyl (1-cyclopentylethylamino)benzoate

→

4'-(1cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone

المذيبات

1,2-dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONTo this solution is added a solution of 5.0 g
2. 2
   درجة الحرارةThe mixture is cooled
3. 3
   workup.ADDITIONpoured onto ice
4. 4
   استخلاصextracted with chloroform
5. 5
   أخرىThe organic layer is separated
6. 6
   غسيلwashed with water and saturated sodium chloride solution
7. 7
   تجفيفdried over anhydrous sodium sulfate
8. 8
   تركيزconcentrated to dryness
9. 9
   أخرىThe crude solid is chromatographed on silica gel
10. 10
    غسيلeluting with methylene chloride

الإجراء التجريبي

A solution of 864 mg. of sodium hydride and 5.3 g. of methylphenylsulfone in 20 ml. of 1,2-dimethoxyethane is stirred at 6° C. for one hour under an atmosphere of argon. To this solution is added a solution of 5.0 g. of methyl (1-cyclopentylethylamino)benzoate in 50 ml. of tetrahydrofuran and the reaction mixture is stirred at 60° C. for 1.5 hours. The mixture is cooled, poured onto ice, acidified with dilute hydrochloric acid and pH 3 and then extracted with chloroform. The organic layer is separated, washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated to dryness. The crude solid is chromatographed on silica gel, eluting with methylene chloride to yield 4'-(1cyclopentylethylamino)-2-(phenylsulfonyl)acetophenone.

المصدر