Reaktion #80817

Reaktionsgleichung

diethyl ether

lithium aluminum hydride

2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline

sodium hydroxide

→

2-hydroxymethyl-2-methyltetrahydroquinoline

Ausbeute 95.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile the reaction temperature was maintained at 40°~45° C
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with brine three times
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate

Vorschrift

To a suspension of lithium aluminum hydride (1.12 g, 29.5 mmol) in THF (10 mL) was added dropwise 2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline (8.88 g, 29.5 mmol) in THF (90 mL) over 25 min, while the reaction temperature was maintained at 40°~45° C. The mixture was heated at 60° C. for 1 h and the excess reagent was decomposed by slow addition of aqueous THF at 0° C. Aqueous sodium hydroxide was added and stirred for 30 min followed by addition of diethyl ether. The organic layer was separated, washed with brine three times, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate to give 4.97 g of 2-hydroxymethyl-2-methyltetrahydroquinoline (95%): 1H NMR (270 MHz, CDCl3) δ6.98 (m, 2H), 6.64 (td, 1H, J=7.3, 1 Hz), 3.73 (bs, 1H), 3.47 (s, 2H), 2.76 (m, 2H), 1.93 (bs, 1H), 1.86 (m, 1H), 1.61 (m, 1H), 1.19 (s, 3H).

Quelle