Diisopropylamine → Lithium diisopropylamide

Participants

Reaction Conditions

Reaction Steps

A solution of lithium diisopropylamide in THF/hexane was prepared from diisopropylamine (0.8 mL, 5.475 mmol) and 2.5M BuLi (2.2 mL, 5.475 mmol) at −50° C. The solution was brought to −10° C. and a hexane solution of 4(4′-propylcyclohexyl)-1-trifluoromethylcyclohexane (1.0 g, 3.65 mmol in 2 mL) was added followed by addition of KtBuO (0.614 mg, 5.475 mmol). The mixture was stirred for 10 min. then brought to RT for 30 min. The reaction was monitored by GCMS for completion. After cooling again to −10° C., the reaction was quenched by addition of water (2 mL), extracted into hexane (10 mL); dried (MgSO4), filtered and the solvent was distilled to obtain the product in 98% yield by GC. The crude product in hexane was filtered through a plug of silica gel to obtain the pure compound, i.e., 4(4′-propylcyclohexyl)-1-difluorovinylcyclohexane.

Provenance & Evidence