Cyclobutanone → HCID 68292161, compound

Participants

Reaction Steps

TMSCN (0.09 mL, 0.70 mmol) was added to a mixture of the compound 30 (90 mg, 0.47 mmol), cyclobutanone (0.05 mL, 0.70 mmol) and 12 (6 mg, 0.05 mmol) with stirring. The reaction mixture was stirred at room temperature for 10 min, and concentrated in vacuo. The residue was diluted with aq Na2SO3, and extracted with DCM. The combined organic layers were washed with aq Na2SO3 and brine, dried over Na2SO4 and concentrated. The residue was purified with silica gel column chromatography using Petroleum ether:Ethyl acetate (10:1) affording to compound 39 (85 mg, 67%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ6.98 (d, 2H, J=8.4 Hz), 6.56 (d, 2H, J=8.4 Hz), 5.39 (br s, 1H), 2.66-2.76 (m, 5H), 2.50 (t, 2H, J=8.4 Hz), 2.28-2.40 (m, 2H), 2.10-2.22 (m, 2H), 2.08 (t, 2H, J=8.4 Hz), 1.80-1.90 (m, 2H).

Provenance & Evidence