Pentane → 5,5,5-Trifluoropentanenitrile

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 6.40 g (50.3 mM) 4,4,4-trifluorobutanol, prepared in Example 45d, and 7.71 ml (55.3 mM) triethylamine in 1.50 ml Et2O at 0° C. under N2, was added 4.28 ml (55.3 mM) methanesulfonyl chloride dropwise. A white precipitate formed and was stirred 60 minutes at 0° C. An equal volume of pentane was added and the reaction mixture was filtered through celite, followed by concentration on a rotary evaporator without heat. The crude mesylate was mixed with 8.19 g (126 mM) KCN and catalytic KI in 150 ml dimethysulfoxide at rt. The reaction mixture was then heated to 80° C. for 3 hours, turning deep orange and gelling. After cooling, the orange gel was poured into 100 ml of stirring H2O, extracted into Et2O, washed with saturated NaCl, dried over MgSO4, filtered and volatiles distilled. The crude liquid residue was 5.12 g (75%).

Provenance & Evidence