Diethyl Ether → 2-(Quinolin-6-yl)propan-2-ol

HRID 449248

Reaktionsgleichung

Reaktionsgleichung von HRID 449248
C[Mg]I.[Mg].[CH3:5]I.[N:7]1[C:16]2[C:11](=[CH:12][C:13](C(OC)=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1.C([O:23][CH2:24][CH3:25])C>>[N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:24]([OH:23])([CH3:25])[CH3:5])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Komponenten

6

Edukt 5

HCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 736812Methyl quinoline-6-carboxylateHCID 5462224MagnesiumHCID 178418373HCID 178418373, Verbindung

Produkt 1

HCID 669948782-(Quinolin-6-yl)propan-2-olAusbeute 84 %

Versuchsvorschrift

To an ice-cold solution of methylmagnesium iodide prepared from magnesium (0.454 g, 18.69 mmol) and methyliodide (1.16 ml, 18.69 mmol) in diethyl ether (15 ml), methyl quinoline-6-carboxylate (0.50 g, 2.67 mmol) in diethyl ether (5 ml) was added and warmed to room temperature. After 12 h, the reaction mixture was cooled to 0° C., quenched with dil. 6N HCl and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under reduced pressure and column chromatographed with ethyl acetate: petroleum ether to afford the title compound as a yellow liquid (0.42 g, 84%). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.83 (dd J=4.2, 1.7 Hz, 1H), 8.34 (dd, J=8.2, 1.1 Hz, 1H), 8.00 (d, J=1.9 Hz, 1H), 7.95 (d, J=8.8 Hz, 1H), 7.88 (dd, J=8.9, 2.0 Hz, 1H), 7.50 (q, J=4.1 Hz, 1H), 5.23 (s, 1H), 1.51 (s, 6H).

Aufarbeitung

  1. additionwas added
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. customquenched with dil. 6N HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under reduced pressure and column
  7. customchromatographed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9e7211fc011d418fa592419e429e4271
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481739B2

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