Reaktion #80749

Reaktionsgleichung

NaOH

water

LiAlH4

2-methoxycarbonylindoline

→

2-hydroxymethylindoline

Ausbeute 96.0%

Lösungsmittel

THF

diethyl ether

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 3.5 h
2. 2
   SonstigeThe organic layer was separated
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated

Vorschrift

To a suspension of LiAlH4 (4.65 g, 0.122 mol) in THF (100 mL) was added dropwise 2-methoxycarbonylindoline (10.85 g, 0.0613 mol) in THF 260 mL at room temperature. The mixture was refluxed for 3.5 h and then excess reagent was decomposed by addition of aqueous THF. To the mixture was added 1N aqueous NaOH (50 mL), water (100 mL), and diethyl ether (100 mL), successively. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated to give 8.77 g of 2-hydroxymethylindoline (96%): 1H NMR (270 MHz, CDCl3) δ7.08 (d, 1H, J=7 Hz), 7.02 (t, 1H, J=7 Hz), 6,71 (t, 1H, J=7 Hz), 6.64 (d, 1H, J=7 Hz), 4.02 (m, 1H), 3.70 (dd, 1H, J=11, 4 Hz), 3.56 (dd, 1H, J=11, 7 Hz), 3.09 (dd, 1H, J=16, 9 Hz), 2.81 (dd, 1H, J=16, 8 Hz).

Quelle