Aluminium lithium hydride → 5-Bromo-1H-indole-3-ethanol

Participants

Reaction Conditions

Reaction Steps

The method of Bascop, S. I.; Laronze, J. Y.; Sapi, J. Synthesis of 2-aminopropyle-3-indole-acetic(propionic) acid derivatives. ARKIVOC 2003, 46-61, was followed. To a solution of ester 12 (4 mmol, 1 equiv) in anhydrous THF (50 mL) was added lithium aluminium hydride (LiAlH4; 16 mmol, 4 equiv) in portions with the temperature maintained at 0° C. The reaction mixture was brought to room temperature and stirred for 30 min. Excess LiAlH4 was destroyed by careful addition of a saturated aqueous solution of Na2SO4 with the temperature maintained at about 0° C. The mixture was filtered and the filtrate washed with THF. The combined filtrates were concentrated under reduced pressure, the residue was acidified to pH 6 with 10% HCl and extracted with CHCl3. The combined organic layer was dried (anhydrous Na2SO4), filtered, evaporated to dryness and purified using flash column chromatography by elution with EtOAc/hexane to give the alcohol 13. Yield: 83%; NMR (300 MHz, CDCl3): δ 2.97 (t, J=18 Hz, 2 H), 3.86-3.93 (m, 2 H), 4.09 (t, J=21 Hz, 1 H), 7.09 (d, J=3 Hz, 1 H), 7.22 (d, J=9 Hz, 1 H), 7.75 (s, 1 H), 8.10 (s, 1 H); MS (APCI): m/z 241.2 [M+H]+.

Provenance & Evidence