Sodium sulfate decahydrate → 2-(2-Methylquinolin-7-yl)propane-1,3-diol

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Reaktionsgleichung

[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([C:24](OCC)=[O:25])[C:19](OCC)=[O:20])=[CH:13][CH:14]=2)[N:9]=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOCC>[CH3:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][C:12]([CH:18]([CH2:24][OH:25])[CH2:19][OH:20])=[CH:13][CH:14]=2)[N:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 1.0 N LAH (15.3 mL, 15.3 mmol) in THF was added diethyl 2-(2-methylquinolin-7-yl)malonate (1.15 g, 3.82 mmol) in Ether (30 mL) slowly at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. Sodium sulfate decahydrate (2.0 g) was added and stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (50 mL). The filtrate was concentrated and the residue obtained was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 40M column, 0-70% CH3CN/water gradient; 30 CV) to give 2-(2-methylquinolin-7-yl)propane-1,3-diol (0.34 g, 1.56 mmol, 41.0% yield) as a solid.

Aufarbeitung

stirringstirred at ambient temperature for 30 minutes
customThe solid was removed by filtration
washwashed with ethyl acetate (50 mL)
concentrationThe filtrate was concentrated
customthe residue obtained
customwas purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

Quellen und Nachweise

ORD-Eintrag: ord-c17a68cf22244f08804d5565569d321b
Quelldatensatz: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08889704B2

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