Ethylene Oxide → 2-(5-indolyl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) mixture of 1.56 g (38.9 mmol) of a 60% dispersion of sodium hydride in 10 mL THF is slowly added a solution of 5.05 g (25.9 mmol) 5-bromoindole (Acros) in 20 mL THF. After H2 evolution stopped (˜10 min) the mixture is cooled to −78° C., and 25.9 mL (64.8 mmol) of a 2.5 M hexane solution of n-butyllithium is added dropwise. After five minutes, added 16.8 mL (38.9 mmol) of a 2.3 M THF stock solution of ethylene oxide and removed cooling bath. After 90 minutes, quenched with 5 mL distilled water. The organic layer is then poured away from the inorganic salts and concentrated. The resulting residue is chromatographed (1:1 hexane:ethyl acetate) to provide 2.24 g of the product as a yellow oil in 54% yield. 1H NMR (CDCl3): δ 2.96 (2H, t, J=6.5 Hz), 3.88 (2H, m), 6.51 (1H, m), 7.06 (1H, dd, J1=8.5 Hz, J2=1.5 Hz), 7.19 (1H, m), 7.33 (1H, d, J=8.5 Hz), 7.49 (1H, s), 8.19 (1H, br). MS (EI) m/z 161 M+, 130 (M−CH2OH)+.

Provenance & Evidence