1-Bromononane → HCID 67329002, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 1.06 g (6.34 mmol) of 4-methoxy-N,N,6-trimethylpyrimidin-2-amine and 1.32 g (6.34 mmol) of 1-bromononane in 20 mL of anhydrous THF were added 5.15 mL (8.34 mmol) of 1.6 M n-BuLi in hexanes. The reaction mixture was stirred at 23° C. for 20 min. The reaction mixture was quenched with saturated aqueous ammonium chloride and poured into 100 mL of water. The compound was extracted with two 80-mL portions of ethyl acetate. The combined organic layer was washed with one 80-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (15×5 cm). Elution with 9:1 hexanes-ethyl acetate afforded the expected product as colorless oil: yield 1.22 g (66%); silica gel TLC Rf 0.7 (9:1 hexanes-ethyl acetate); 1H-NMR (CDCl3) δ 0.85 (t, 3H, J=6.8 Hz), 1.28-1.23 (br m, 14H), 1.82 (quint, 2H, J=7.2 Hz), 2.46 (dd, 2H, J=7.6, 7.6 Hz), 3.14 (s, 6H), 3.85 (s, 3H) and 5.77 (s, 1H); 13C NMR (CDCl3) δ 14.09, 22.66, 28.46, 29.31, 29.32, 29.48, 29.54, 29.59, 31.88, 36.78, 37.83, 37.83, 52.75, 93.03, 162.29, 170.25 and 173.93.

Provenance & Evidence