反应详情

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.

1. additionwas added
2. dissolutionMost of the solid dissolved
3. waitThe stirring was continued for 27 hours
4. customThe layers were separated
5. extractionThe aqueous layer was extracted with ether (2×75 mL)
6. washThe combined ether phases were washed with 50 mL of brine
7. dry with materialdried over MgSO4
8. customEvaporation of the solvent
9. waitleft 9.17 g of orange oil
10. customThe oil was chromatographed on a 700 g column of silica gel
11. washThe column was eluted with 1:2 CH2Cl2 -Skellysolve B and 200 mL fractions
12. customwere collected