Ethyl Bromide → 7-Ethoxy-2-methylquinoline

HRID 339049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339049
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:20][CH3:21]>CN1C(=O)CCC1>[CH2:20]([O:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH3:1])=[N:3]2)=[CH:8][CH:7]=1)[CH3:21]

Komponenten

5

Edukt 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 1354519692-Methylquinolin-7-ol

Produkt 1

HCID 867075387-Ethoxy-2-methylquinolineAusbeute 88,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-methylquinolin-7-ol (400 mg, 2.51 mmol), Cs2CO3 (2.46 g, 7.54 mmol) and NMP (12 mL) was added bromoethane (0.563 mL, 7.54 mmol). The reaction mixture was stirred at ambient temperature overnight. The reaction was partitioned between ether and water. The aqueous layer was extracted with ether. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (2:1 to 5:1 hexanes:EtOAc) to give 7-ethoxy-2-methylquinoline (416 mg, 88%).

Aufarbeitung

  1. customThe reaction was partitioned between ether and water
  2. extractionThe aqueous layer was extracted with ether
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (2:1 to 5:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-10c8578d969a46b094202a0b360964fb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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