Methanol → HCID 21993984, compound

Participants

Reaction Conditions

Reaction Steps

To 10.757 g (43.676 mM) of ethyl 5-thia-1,8b-diazaacenaphthylene-4-carboxylate in 200 ml of dichloromethane was added a 20 ml (approx.) portion of 87.4 ml (131 mM) of 1.5M diisobutylaluminum hydride-toluene at −78° C. and the temperature was increased to about 0° C. After this mixture was cooled to −78° C. again, about 30 ml of 1.5M diisobutylaluminum hydride-toluene was added and the temperature was increased to about 0° C. This reaction mixture was further cooled to −78° C. and the remainder of 1.5M diisobutylaluminum hydride-toluene was added. The mixture was stirred at the prevailing temperature for 0.5 hour. To this reaction mixture was added methanol at −78° C. to decompose the excess diisobutylaluminum hydride. Then, water was added with caution under ice-cooling until a precipitate had formed. The precipitate was filtered off with the aid of celite and washed with aqueous dimethyl sulfoxide. From the pooled filtrate, the solvent was distilled off under reduced pressure and the solid residue was rinsed with diethyl ether to provide the title compound.

Provenance & Evidence