Allyl bromide → HCID 67377459, compound

Participants

Reaction Steps

To a solution of 23 (250 mg, 0.92 mmol) in anhydrous THF (20 mL), NaH (60% in mineral oil, 44 mg, 1.098 mmol), allyl bromide (133 mg, 1.10 mmol) and tetrabutylammonium bromide (354 mg, 1.10 mmol) were added under argon atmosphere. The mixture was stirred for 15 h at room temperature. After removal of the solvent, the residue was diluted with H2O (20 mL) and extracted with CH2Cl2 (3×20 mL). The CH2Cl2 extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography using CH2Cl2/EtOAc (4/1, v/v) as eluent to afford compound 30 (156 mg, yield: 54%); as an oil; 1H NMR (400 MHz, CDCl3) δ 2.40 (s, 3H), 3.92 (m, 2H), 4.70 (m, 1H), 5.22 (m, 2H), 5.93 (m, 1H), 6.25 (d, 1H, J=7.3 Hz), 7.21 (s, 1H), 7.75 (d, 1H, J=7.3 Hz); 13C NMR (100 MHz, CDCl3) δ 14.5, 46.6, 64.3, 100.7, 109.1, 116.8, 125.7, 134.5, 142.7, 145.8, 146.3. Anal. Calcd for C11H12IN3: C, 42.19; H, 3.86; N, 13.42. Found: C, 42.39; H, 3.95; N: 1328.

Provenance & Evidence