반응 #5697

반응 방정식

benzyl chloride

5-fluoroindole

18-crown-6

potassium tert-butoxide

→

1-benzyl-5-fluoroindole

수율 14.1%

용매

Water

ether

ether

ether

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The layers were separated
3. 3
   추출The aqueous layer was extracted with 100 ml of ether
4. 4
   세척The combined ether layers were washed with 50 ml of brine
5. 5
   건조dried over MgSO4
6. 6
   기타Evaporation of the solvent
7. 7
   workup.WAITleft 6.95 g of orange oil
8. 8
   기타The oil was chromatographed on a 600 g column of silica gel
9. 9
   세척The column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions
10. 10
    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 3.27 g (29.14 mmoles) of potassium tert-butoxide. The mixture was stirred while a solution of 3.75 g (27.75 mmoles) of 5-fluoroindole in 80 ml of ether was added. The stirring was continued for 0.5 hour. Solid was present. Then 3.69 g (29.15 mmoles) of benzyl chloride in 80 ml of ether was added. The mixture was stirred for 28 hours. Water (100 ml) was added. The layers were separated. The aqueous layer was extracted with 100 ml of ether. The combined ether layers were washed with 50 ml of brine and dried over MgSO4. Evaporation of the solvent left 6.95 g of orange oil. The oil was chromatographed on a 600 g column of silica gel. The column was eluted with 30% CH2Cl2 -Skellysolve B and 200 ml fractions were collected. The fractions were assayed by silica gel tlc (1×4") (30% CH2Cl1 -Skellysolve B). Fractions 11-15 were combined giving 0.88 g (14%) of 1-benzyl-5-fluoroindole as a pale yellow oil which contained a small amount of 1,3-dibenzyl-5-fluorindole.

출처