4-Chlorobenzaldehyde → 5-(4-chlorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline

HRID 1501303

Reaktionsgleichung

Reaktionsgleichung von HRID 1501303
CO[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[CH:8]2.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.FC(F)(F)S(O[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Si](C)(C)C)(=O)=O.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>C1COCC1>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[O:19][CH:10]3[CH:9]=[CH:8][C:7]4[C:12]([N:11]3[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]2=3)=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:16][CH:15]=1

Komponenten

7

Edukt 5

HCID 77264-ChlorobenzaldehydeHCID 2855718-Crown-6HCID 703108-MethoxyquinolineHCID 522689Potassium FluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

Produkt 1

HCID 1185493035-(4-chlorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinolineAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the general procedure, treatment of 8-methoxyquinoline (0.086 g, 0.50 mmol) and 4-chlorobenzaldehyde (0.105 g, 0.75 mmol) with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (0.179 g, 146 μL, 0.60 mmol) in the presence of KF (0.070 g, 1.2 mmol) and 18-crown-6 (0.317 g, 1.2 mmol) in THF (2.0 mL) at −10° C. to room temperature for 12 hrs followed by flash column chromatography (Pet. ether/EtOAc=70/30) of the crude reaction mixture afforded 5-(4-chlorophenyl)-5H,6aH-benzo[4,5][1,3]oxazino[3,2-a]quinoline as inseparable mixture of diastereomers as a white solid (0.121 g, 65% yield, dr determined by 1H NMR analysis of crude reaction mixture is 1:1).

Aufarbeitung

  1. customat −10° C. to room temperature
  2. customfor 12 hrs
  3. customreaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-4af32e05559945108bd2a53ed002fcfe
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206196B1

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