Diisopropylamine → HCID 59545180, compound

Participants

Reaction Conditions

Reaction Steps

A dry-ice-acetone cooled 250 mL-RB flask is charged with anhydrous THF (30 ml) and diisopropylamine (2.2 g, 0.022 mol). A solution of butyl lithium in hexanes (1.6 M, 16 ml, 0.025 mol) is added over 30 minutes. After stirring at −78° C. for an additional 30 minutes, the mixture is warmed up to 0° C. and stirred for an hour. The mixture is cooled again in a dry-ice-acetone bath, and anhydrous ethyl acetate (1.76 g, 0.02 mol) is added dropwise over 30 minutes. After the mixture is stirred at −78° C. for 30 minutes, diisopropylsilanediyl bis(trifluoromethanesulfonate) (4.12 g, 0.01 mol) is added dropwise over 10 minutes. The reaction is quenched with water, and poured into ice-water. The organic layer is separated, and the aqueous layer is extracted with ether. The combined organic solution is washed with brine, dried over sodium sulfate, filtered, and the filtrate concentrated. The residue is purified by distillation in a Kugelrohr to yield 1.15 g (40%) of product as a yellowish oil. 1H NMR (500 MHz, CDCl3, in ppm) δ 4.09 (q, 4H, J=7.0 Hz), 1.99 (s, 4H), 1.24 (t, 6H, J=7.0 Hz), 1.12 (heptet, 2H, J=6.5 Hz), 1.06 (d, 12H, J=6.5 Hz).

Provenance & Evidence