Diisobutylaluminum hydride → HCID 89544619, compound

Participants

Reaction Conditions

Reaction Steps

1-(3,5-Difluoro-4-pyridyl)cyclopropanecarbonitrile (3.74 g, 20.8 mmol) was dissolved in Toluene (69.2 mL). At −10° C. DIBAL-H in Toluene 1.0M (43.6 mL, 43.6 mmol) was added dropwise to the yellow solution. The reaction mixture was stirred 30 min at −10° C. The mixture was then cooled down to −65° C. At −65° C. NaBH4 (4.81 g, 125 mmol) was added, then carefully 50 mL MeOH. The reaction mixture was stirred 1 h at −50° C., after approximately 30 min a sudden and strong gas evolution occurred and the temperature rose to −30° C. The reaction mixture was poured into 200 mL of 1M potassium sodium tartrate. The pale yellow solution was extracted 3 times with Ether. The combined organic phases were washed with brine and dried with Na2SO4, filtrated and the filtrate evaporated that gave a colorless mixture of oil and solid (3.95 g). The residue was dissolved in Ether and extracted with 4N HCl. The water layer was put to pH=10 with NaOH 30% in water until a white suspension appeared. The suspension was filtrated and washed with ether. The water layer from the filtrate was extracted 3 times with ether. The combined organic layers were dried with Na2SO4, filtrated and evaporated. The residue was a colorless mixture of oil and solid. The mixture was triturated with Ether and the solid was filtrated, the filtrate evaporated which gave the desired product as colorless oil (1.383 g).

Provenance & Evidence