تفاعل #5695

معادلة التفاعل

indole

allyl bromide

18-crown-6

potassium tert-butoxide

→

1-allylindole

المردود 74.0%

المذيبات

Water

ether

ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISSOLUTIONAll of the solid did not dissolve
3. 3
   workup.WAITThe stirring was continued for 67.5 hours
4. 4
   أخرىThe layers were separated
5. 5
   استخلاصThe aqueous layer was extracted with ether (2×75 ml)
6. 6
   غسيلThe combined ether phases were washed with 50 ml of brine
7. 7
   تجفيفdried over MgSO4
8. 8
   أخرىEvaporation of the solvent
9. 9
   workup.WAITleft 16.02 g of brown oil
10. 10
    أخرىThe oil was chromatographed on a 1100 g column of silica gel
11. 11
    غسيلThe column was eluted with 10% acetone-Skellysolve B and 2200 ml fractions
12. 12
    أخرىwere collected

الإجراء التجريبي

To a solution of 2.39 g (9.04 mmoles) of 18-crown-6 in 250 ml of dry ether was added 13.1 g (116.7 mmoles) of potassium tert-butoxide. The mixture was stirred while 11.72 g (100 mmoles) indole was added. The stirring was continued for 3 hours. All of the solid did not dissolve. Then 14.1 g (116.5 mmoles) of allyl bromide in 100 ml of ether was added during 0.5 hour. The stirring was continued for 67.5 hours. Water (200 ml) was added. The layers were separated. The aqueous layer was extracted with ether (2×75 ml). The combined ether phases were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 16.02 g of brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 10% acetone-Skellysolve B and 2200 ml fractions were collected. The fractions were assayed by silica gel tlc (1×4") (10% acetone-Skellysolve B). Fractions 17-23 were combined giving 11.60 g (74%) of 1-allylindole as a yellow brown oil.

المصدر