Diisopropylamine → HCID 14347486, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of diisopropylamine (4.02 mL) in dry tetrahydrofurane (30 mL) under argon was treated dropwise with 1.6M n-butyl lithium in hexane (18 mL). The reaction was kept at -5° C. during the addition and for 15 minutes thereafter, then it was cooled to -78° C. and a solution of 2,2'-bis(trifluoromethyl)benzophenone (8.0 g) in tetrahydrofurane was added at such a rate that the reaction temperature did not exceed -65° C. The mixture was stirred at -78° C. for 10 minutes, then it was allowed to slowly equilibrate to room temperature over 30 minutes. After the solvents were removed under reduced pressure, the residue was treated with water (100 mL) and the resulting solid was filtered off, washed with water and dried. Crystallization of the solid from dichloromethanehexane furnished 7.72 g of 3-hydroxy-3,3-bis[2-(trifluoromethyl)phenyl]-propanenitrile, mp 168°-170° C. A sample was recrystallized from the same solvent system to give the analytical specimen, mp 171°-172° C. Anal. Calculated for C17H11F6NO: 56.83: H, 3.08: F, 31.73: N, 3.80. Found: C. 56.87; H, 2.81: F, 31.88: N, 4.14.

Provenance & Evidence