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

HRID 37960

반응식

HRID 37960 반응식
[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

참가 물질

6

반응물 4

HCID 240BenzaldehydeHCID 887Methanol2회HCID 351795Indole-3-acetonitrileHCID 10942334Sodium Methoxide

생성물 1

HCID 666408512-1H-indol-3-yl-3-phenylacrylonitrile수율 44.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-fdec3f07fd6b4143adf388cd951261cd
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524704B2

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