Dimethylformamide → HCID 22040099, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi (7.56 mL, 18.9 mmol, 2.5M in hexanes) followed by DMF (5.5 mL) were added to a cooled −78° C. solution of 1-benzyloxy-2-bromo-4-ethyl-benzene (5 g, 17.2 mmol) in THF (40 mL). The reaction was stirred at −78° C. for 1 hr and then warmed up to rt. After 2 hrs the reaction was quenched with 1N HCl and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a yellow oil. Purification by flash column chromatography (0% to 5% EtOAc in hexanes) gave the title compound as a clear oil (3.6 g, 87%). 1H NMR (400 MHz, CDCl3): δ 1.22 (t, J=7.8 Hz, 3 H), 2.62 (q, J=7.8 Hz, 2 H), 5.17 (s, 2 H), 6.97 (d, J=8.6 Hz, 1 H), 7.33–7.45 (m, 6 H), 7.69 (s, 1 H), 10.54 (s, 1 H).

Provenance & Evidence