Indole → 1-(4-Chlorobenzyl)-1h-indole

HRID 5593

反応式

HRID 5593 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.[OH-].[K+]>O.C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 798IndoleHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14797Potassium Hydroxide

生成物 1

HCID 9671631-(4-Chlorobenzyl)-1h-indole収率 84.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

A mixture of 11.72 g (0.1 mole) of indole, 17.71 g (0.11 mole) of 4-chlorobenzyl chloride, 33 g (0.5 mole) of 85% KOH, 14 mL of H2O, 2.5 g (2.5 mmoles) of PEG-1000 and 100 mL of toluene was stirred and heated at 55°-65° for 22 hours. After cooling to room temperature, 50 mL of H2O was added. The layers were separated. The aqueous layer was extracted with 100 mL of toluene. The combined organic phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 29 g of orange-brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 1:1 CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 12-19 were combined giving 23.11 g of crude product as a pink oil The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed as before. Fractions 20-30 were combined giving 20.33 g (84%) of 1-(4-chlorobenzyl)indole as a yellow oil.

後処理

  1. temperatureheated at 55°-65° for 22 hours
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 mL of toluene
  4. washThe combined organic phases were washed with 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. waitleft 29 g of orange-brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. washThe column was eluted with 1:1 CH2Cl2 -Skellysolve B and 200 mL fractions
  10. customwere collected
  11. customFractions 12-19 were combined giving 23.11 g of crude product as a pink oil The oil
  12. customwas chromatographed on a 1100 g column of silica gel
  13. washThe column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
  14. customwere collected

出典と根拠

ORDレコード
ord-0aa88ee7cb854783bfc493ea25668c80
出典データセット
uspto-grants-1993_09
特許番号
US05245046

関連ノート

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