تفاعل #528794

معادلة التفاعل

p-toluenesulfonic acid

tryptophol

5-chloro-2-pentanone

→

1-(3-chloropropyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةof refluxing
2. 2
   workup.ADDITION400 mg more of acid is added
3. 3
   أخرىAfter a total of 2 hr
4. 4
   درجة الحرارةthe reaction is cooled
5. 5
   ترشيحfiltered
6. 6
   غسيلwashed with 5% sodium bicarbonate, water
7. 7
   تجفيفdried over sodium sulfate
8. 8
   أخرىEvaporation under reduced pressure
9. 9
   أخرىaffords an oil
10. 10
    أخرىThis oil is purified by chromatography on silica gel
11. 11
    غسيلElution with benzene and concentration of the eluent

الإجراء التجريبي

To a solution of tryptophol (15 g, 0.09 M) in 150 ml of benzene, 5-chloro-2-pentanone (12 g, 0.10 M) is added. The mixture is heated in the presence of 200 mg of p-toluenesulfonic acid and hydrated alkali-aluminum silicate (Molecular Sieves No. 4). After 1 hr. of refluxing, 400 mg more of acid is added. After a total of 2 hr. the reaction is cooled, filtered and washed with 5% sodium bicarbonate, water and dried over sodium sulfate. Evaporation under reduced pressure affords an oil. This oil is purified by chromatography on silica gel. Elution with benzene and concentration of the eluent gives 1-(3-chloropropyl)-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole, nmr (CDCl3) δ1.33 (3H); 1.93 (4H), 2.75 (2H).

المصدر