Diisobutylaluminum hydride → HCID 58432985, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 14 (359 mg) in 4 ml of THF is cooled to −78° C. under N2 and to this is added 1.5 ml of DIBALH (1M in hexane). After stirring for 30 min at −78° C., only starting material is observed. The iPrOH/CO2 bath is replaced for an ice bath and stirring is continued at 0° C. for 2 h. TLC shows complete conversion. The mixture is re-cooled to −78° C. and the reaction mixture is quenched with 1N HCl (5 ml). The cooling bath is removed and the reaction mixture is diluted with 1N HCl (50 ml) and EtOAc (50 ml). The layers are separated and the organic layer is washed once more with 1N HCl (50 ml). The organic layer is washed with brine, dried and concentrated. 286 mg of 15 are obtained as a white solid with melting point: 148-149° C.

Provenance & Evidence