Methanol → HCID 21993984, compound

Temperature

0 °C

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.

1. temperatureAfter this mixture was cooled to −78° C. again
2. temperaturethe temperature was increased to about 0° C
3. temperatureThis reaction mixture was further cooled to −78° C.
4. temperaturecooling until a precipitate
5. customhad formed
6. filtrationThe precipitate was filtered off with the aid of celite
7. washwashed with aqueous dimethyl sulfoxide
8. distillationFrom the pooled filtrate, the solvent was distilled off under reduced pressure
9. washthe solid residue was rinsed with diethyl ether

ORD record

ord-610af9a6495c4a8696886f22caa3d3b5

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235731B1