Ethyl Acetate → HCID 21071406, Verbindung

HRID 1666849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666849
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:6]=[C:5]2[CH2:21][CH2:22][N:23]1[C:31](=[O:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]1=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:41][CH2:42][CH3:43].CCOC(C)=O>CN(C=O)C>[CH2:41]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([Si:11]([CH:12]([CH3:14])[CH3:13])([CH:18]([CH3:19])[CH3:20])[CH:15]([CH3:16])[CH3:17])[CH:6]=[C:5]2[CH2:21][CH2:22][N:23]1[C:24](=[O:33])[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:31]1=[O:32])[CH2:42][CH3:43]

Komponenten

6

Edukt 4

HCID 8857Ethyl Acetate2×HCID 10796Cesium carbonateHCID 336431-IodopropaneHCID 21071403HCID 21071403, Verbindung

Produkt 1

HCID 21071406HCID 21071406, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Combine 2-(2-(5-hydroxy-1-triisopropylsilanyl-1H-indol-3-yl)ethyl)isoindole-1,3-dione (0.7 g, 1.5 mmol), cesium carbonate (1 g, 3 mmol) and 1-iodopropane (0.4 g, 2.3 mmol) in DMF (25 mL) and stir at ambient temperature overnight Pour the reaction mixture into 50% EtOAc in hexanes and wash three times with brine. Dry the organic layer over MgSO4 and concentrate under vacuum to give an oil. Chromatograph the oil on silica gel eluting with 5% EtOAc in hexanes to give the title compound: ISMS 505 (M+1); 1H NMR (CDCl3) 7.80-7.78 (m, 2H), 7.67-7.65 (m, 2H), 7.30-7.27 (d, 1H), 7.12-7.11 (d, 1H), 7.02 (s, 1H), 6.77-6.74 (m, 1H), 4.01-3.96 (m, 4H), 3.12-3.08 (m; 2H), 1.86-1.81 (m, 2H), 1.64-1.57 (m, 3H), 1.08-1.04 (m, 21H).

Aufarbeitung

  1. washwash three times with brine
  2. dry with materialDry the organic layer over MgSO4
  3. concentrationconcentrate under vacuum
  4. customto give an oil

Quellen und Nachweise

ORD-Eintrag
ord-661066ef8ab34005b2b813c820332e7a
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044090B2

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