2-Methylindole → 1-Benzyl-2-methylindole

HRID 5597

反応式

HRID 5597 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>O.C1(C)C=CC=CC=1>[CH2:11]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 72242-MethylindoleHCID 7503Benzyl ChlorideHCID 14797Potassium Hydroxide

生成物 1

HCID 33071511-Benzyl-2-methylindole収率 9.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

A mixture of 13.11 g (0.1 mole) of 2-methylindole, 13.92 g (0.11 mole) of benzyl 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 60° for 23 hours. After cooling to room temperature, 100 mL of H2O was added. The layers were separated. The aqueous layer was extracted with 100 mL of toluene. The combined toluene phases were washed 2N HCl (2×50 mL), H2O (2×50 mL), and 50 mL of brine and dried over MgSO4. Evaporation of the solvent left 26.98 g of dark brown 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 by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 20-22 were combined giving 2.08 g (9%) of 1-benzyl-2-methylindole as a yellow oil which solidified.

後処理

  1. temperatureheated at 60° for 23 hours
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with 100 mL of toluene
  4. washThe combined toluene phases were washed 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 26.98 g of dark brown oil
  8. customThe oil was chromatographed on a 1100 g column of silica gel
  9. washThe column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
  10. customwere collected

出典と根拠

ORDレコード
ord-1e9c28188ba44ba1b3e90f556b1d3cd8
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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