Diisobutylaluminum hydride → 2-(1H-indol-2-yl)ethanol

Participants

Reaction Steps

Ester 4-1 (0.54 g, 2.6 mmol) was dissolved in 13 mL CH2Cl2 at -78°, and DIBAL (1M in CH2Cl2, 5.8 ml, 5.8 mmol) was added dropwise. The mixture was stirred at -78° for 15 min then warmed to RT for 30 min and quenched in sat. aqueous Na/K tartrate. This solution was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), and concentrated. Flash chromatography (silica 50% EtOAc/hexane) provided 4-2 as a brown oil. Rf 0.38 (silica, 50% EtOAc/hexane).

Provenance & Evidence