Methanol → HCID 71279125, compound

Participants

Reaction Conditions

Reaction Steps

To lithium borohydride (2M solution in THF, 629 μL, 1.26 mmol) was added dropwise trimethylchlorosilane (273 mg, 321 μL, 2.51 mmol) over a period of 5 min at 0-5° C. At that temperature a solution of 2-(4-methyl-1-phenyl-1H-pyrazol-3-yl)acetonitrile (62 mg, 314 μmol) in THF (0.5 mL) was added dropwise. The mixture was stirred at 70° C. for 1.5 h. After cooling down to 0-5° C., MeOH (0.5 mL) was added dropwise. After 10 min the ice bath was removed and the mixture was allowed to warm up to RT. The reaction mixture was poured into NaOH (1 M, 10 mL) and extracted with dichloromethane (3×25 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give the product as light yellow semisolid (46 mg, 206 μmol, 65.4%) which was used without further purification for the next step.

Provenance & Evidence