Benzaldehyde → 2-1H-indol-3-yl-3-phenylacrylonitrile

HRID 37960

反応式

HRID 37960 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.CO.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[O-].[Na+]>C(Cl)Cl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[CH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]#[N:12])=[CH:2]1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 887Methanol2 回HCID 351795Indole-3-acetonitrileHCID 10942334Sodium Methoxide

生成物 1

HCID 666408512-1H-indol-3-yl-3-phenylacrylonitrile収率 44.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(1H-Indol-3-yl)-3-phenylacrylonitrile was prepared by the addition of 3-indolylacetonitrile (2.02 g, 12.9 mmol), MeOH (18 mL), benzaldehyde (1.60 mL, 15.5 mmol), and a 25% wt solution of sodium methoxide in MeOH (3.2 mL, 14.2 mmol) to a 50 mL flask. The solution was allowed to stir at ambient temperature under N2 for 16 h. The reaction solution was diluted with DCM (20 mL), molecular sieves (250 mg) were added, and the solution was allowed to reflux for 1 hour. The reaction was quenched with the addition of sat. NH4Cl (20 mL). The organic phase was partitioned, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was chromatographed (SiO2, 100% hexane to 5% EtOAc) to yield 1.4 g (44% yield) of 2-1H-indol-3-yl-3-phenyl-acrylonitrile; 1H NMR (CDCl3) δ 8.42 (1H, br s), 7.97 (1H, d), 7.87 (2H, m), 7.63 (1H, s), 7.60 (1H, d), 7.37-7.48 (4H, m), 7.25-7.33 (2H, m); TLC (SiO2 plate, 5:1 hexane/EtOAc) Rf=0.35; MS (ESI): 245 (MH+).

後処理

  1. additionwere added
  2. temperatureto reflux for 1 hour
  3. customThe reaction was quenched with the addition of sat. NH4Cl (20 mL)
  4. customThe organic phase was partitioned
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude material was chromatographed (SiO2, 100% hexane to 5% EtOAc)

出典と根拠

ORDレコード
ord-fdec3f07fd6b4143adf388cd951261cd
出典データセット
uspto-grants-2013_09
特許番号
US08524704B2

関連ノート

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