吲哚 → 1 -(烯丙基)吲哚

HRID 5599

反应方程式

HRID 5599 反应方程式
C1OCCOCCOCCOCCOCCOC1.[CH3:19][C:20](C)([O-])[CH3:21].[K+].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1.C(Br)C=C>CCOCC.O>[CH2:21]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1)[CH:20]=[CH2:19]

参与物

7

反应物 4

HCID 798吲哚HCID 78413-溴丙烯HCID 2855718-冠醚-6HCID 23665647叔丁醇钾

产物 1

HCID 856251 -(烯丙基)吲哚收率 74%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 3283乙醚溶剂2 次

实验过程

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.

后处理

  1. additionwas added
  2. dissolutionAll of the solid did not dissolve
  3. waitThe stirring was continued for 67.5 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 16.02 g of brown oil
  10. customThe oil was chromatographed on a 1100 g column of silica gel
  11. washThe column was eluted with 10% acetone-Skellysolve B and 2200 ml fractions
  12. customwere collected

来源与证据

ORD记录
ord-a27889ee44e040db9dcdb94b80457c09
来源数据集
uspto-grants-1993_09
专利号
US05245046

关联笔记

加载中…