Diisopropylamine → HCID 59545179, compound

Participants

Reaction Conditions

Reaction Steps

A dry-ice-acetone cooled 500 mL-RB flask is charged with anhydrous THF (90 ml) and diisopropylamine (6.7 g, 0.066 mol). A solution of butyl lithium in hexanes (1.6 M, 48 ml, 0.075 mol) is added over 1 hour. After stirring at −78° C. for an additional 30 minutes, the mixture is warmed to 0° C. and stirred for an hour and at room temperature for 15 minutes. The mixture is cooled again in a dry-ice acetone bath, and anhydrous ethyl acetate (5.28 g, 0.06 mol) is added dropwise over 30 minutes. After the mixture is stirred at −78° C. for 1 hour, diisobutylsilanediyl bis(trifluoromethanesulfonate) (14.4 g, 0.01 mol) is added dropwise over 30 minutes. After about 4 hours, 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 flash column chromatography on silica gel yield 2.6 g (27%) of product as a yellowish oil. 1H NMR (500 MHz, CDCl3, in ppm) δ 4.10 (q, 4H, J=7.0 Hz), 2.03 (s, 4H), 1.82-1.92 (theptat, 2H, J=6.5 Hz, 6.5 Hz), 1.25 (t, 6H, J=7.0 Hz), 0.96 (d, 12H, J=6.5 Hz), 0.75 (d, 4H, J=6.5 Hz).

Provenance & Evidence