Dimethylformamide → HCID 86593857, compound

Participants

Reaction Conditions

Reaction Steps

TMEDA (23.0 g, 0.198 mol), 1,3-di(3,3-dimethylbutoxy)benzene (46.2 g, 0.166 mol) and ether (500 mL) were brought together in a two-neck 1-L flask fitted with a nitrogen inlet and a pressure-equalizing addition funnel. The reaction mixture was cooled to 0° C., and deaerated. n-BuLi (2.5 M solution in hexanes, 0.18 mol) was added dropwise over a period of 30 min via the addition funnel. The mixture was stirred for 3 h, following which that time it was warmed to room temperature. At this point DMF (23.0 g, 0.315 mol) was added dropwise; after 2 h of stirring, the reaction was quenched with water, extracted with ether (4×300 mL), separated, and evaporated. The product was purified by chromatography on silica using 9:1 hexanes:ethyl acetate as the eluant, giving 36.6 g of product (72% yield, based on 46.2 g of the 1,3-di(3,3-dimethylbutoxy)benzene starting material). 1H NMR (250 MHz, CDCl3): 10.49 (s, 1H), 7.37 (t, 1H, J=8.5 Hz), 6.52 (d, 2H, J=8.5 Hz), 4.06 (t, 4H, J=7.2 Hz), 1.76 (t, 4H, J=7.2 Hz), 0.96 (s, 18H). HRMS (ESI+) m/z: 329.2107 (calcd for C19H30O3Na (M+Na)+ 329.2092).

Provenance & Evidence