Tetrahydrofuran → 1-(Pyridin-2-yl)cyclobutane-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

In a dry flask under Ar, 2-fluoropyridine (3.18 ml, 37 mmol) and cyclobutanecarbonitrile (3.0 g, 37 mmol) were dissolved in toluene (55 mL). The solution was cooled to 0° C. A 1M solution of sodium bis(trimethylsilyl)amide in THF (40.7 mL, 40.7 mmol) was added slowly over 5 min. After 1 h, the solution was warmed to room temperature. After another 19 h, the reaction was diluted with NH4Cl (aq) and DCM. The layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were dried over MgSO4, filtered and concentrated to yield 4.68 g (80%) of 1-pyridin-2-yl-cyclobutanecarbonitrile as a pale yellow oil, m/z=159.7 [M+1]+.

Provenance & Evidence