反応 #80817

反応方程式

diethyl ether

lithium aluminum hydride

2-methyl-N-trifluoroacetyl-2-methoxycarbonyltetrahydroquinoline

sodium hydroxide

→

2-hydroxymethyl-2-methyltetrahydroquinoline

収率 95.0%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   温度while the reaction temperature was maintained at 40°~45° C
2. 2
   その他The organic layer was separated
3. 3
   洗浄washed with brine three times
4. 4
   乾燥dried over magnesium sulfate
5. 5
   濃縮concentrated
6. 6
   その他The residue was purified by silica gel column chromatography with 3:1 hexane/ethyl acetate

実験手順

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).

出典