Sodium sulfate decahydrate → 2-Methyl-2-(2-methylquinolin-8-yl)propan-1-ol

HRID 338906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338906
[CH3:1][C:2]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)([CH3:7])[C:3](OC)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][C:2]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)([CH3:1])[CH2:3][OH:4]

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 70984004Methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate

Produkt 1

HCID 709839442-Methyl-2-(2-methylquinolin-8-yl)propan-1-olAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate (0.57 g, 2.3 mmol) in THF (10 mL) was added 1 N LAH (5.9 mL, 5.9 mmol) in THF at 0° C. and stirred at 0° C. for 6 hours. Sodium sulfate decahydrate (2.0 g) was added and the reaction mixture was stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (30 mL). The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate) to give 2-methyl-2-(2-methylquinolin-8-yl)propan-1-ol (0.43 g, 85%) as an oil.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at ambient temperature for 30 minutes
  2. customThe solid was removed by filtration
  3. washwashed with ethyl acetate (30 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-e7f3f4e6e1a24344a3ee18d971539c0b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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