Diisopropylamine → Ethyl 2-butylhexanoate

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (45.5 g, 450 mmol) was dissolved in anhydrous THF 150 mL and cooled to −40° C. in an acetonitrile/dry ice bath under nitrogen protection. 2.5M n-butyllithium (n-BuLi)/hexane solution (126 mL, 315 mmol) was added with stirring. After the addition, the mixture was kept in the ice water bath for 30 minutes, cooled down to −78° C. in an acetone/dry ice bath, and ethylhexanoate (43.3 g, 300 mmol) was added dropwise. The reaction mixture was stirred at the same temperature for 1 hour and then, iodobutane (60.7 g, 330 mmol) in 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (11.5 g, 90 mmol) was added dropwise. The resulting solution was warmed to −40° C., stirred for 2 hours, and kept at room temperature overnight. The reaction mixture was quenched with a saturated NH4Cl aqueous solution, and concentrated via rotary evaporation. Into the flask, 200 mL of Et2O and 200 mL of water were added. After acidification of the mixture using a 2N HCl aqueous solution, the organic layer was separated, washed with 10% (v/v) HCl aqueous solution (150 mL×2), and concentrated via rotary evaporation. The resulting crude yellow oil was purified via vacuum distillation. The compound 16 was collected as colorless oil (45.0 g, 75%). 1H NMR (CDCl3): δ 0.86-0.90 (6H, m), 1.07-1.62 (12H, m), 1.25 (3H, t), 2.27-2.32 (1H, m), 4.12 (2H, q). MS (EI): calcd, 200.3. found M+H+, 201.2.

Provenance & Evidence