반응 #5692

반응 방정식

5-chloroindole

benzyl bromide

18-crown-6

potassium tert-butoxide

→

1-benzyl-5-chloroindole

수율 90.0%

용매

Water

ether

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.DISSOLUTIONMost of the solid dissolved
3. 3
   workup.WAITThe stirring was continued for 27 hours
4. 4
   기타The layers were separated
5. 5
   추출The aqueous layer was extracted with ether (2×75 mL)
6. 6
   세척The combined ether phases were washed with 50 mL of brine
7. 7
   건조dried over MgSO4
8. 8
   기타Evaporation of the solvent
9. 9
   workup.WAITleft 9.17 g of orange oil
10. 10
    기타The oil was chromatographed on a 700 g column of silica gel
11. 11
    세척The column was eluted with 1:2 CH2Cl2 -Skellysolve B and 200 mL fractions
12. 12
    기타were collected

실험 절차

To a solution of 0.8 g (3.03 mmoles) of 18-crown-6 in 100 mL of dry ether was added 4.39 g (39.12 mmoles) potassium tert-butoxide. The mixture was stirred while 5.08 g (33.51 mmoles) of 5-chloroindole was added. The stirring was continued for 0.5 hour. Most of the solid dissolved. Then 6.69 g (39.11 mmoles) of benzyl bromide in 40 mL of ether was added during 0.5 hours. The stirring was continued for 27 hours. Water (100 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 9.17 g of orange oil. The oil was chromatographed on a 700 g column of silica gel. The column was eluted with 1:2 CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (2×8") (1:2 CH2Cl2 -Skellysolve B). Fractions 10-14 were combined giving 7.26 g (90%) of 1-benzyl-5-chloroindole as a yellow oil.

출처