반응 #80817

반응 방정식

diethyl ether

lithium aluminum hydride

2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline

sodium hydroxide

→

2-hydroxymethyl-2-methyltetrahydroquinoline

수율 95.0%

용매

THF

THF

THF

반응 조건

후처리

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

실험 절차

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).

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