Dibutyltin oxide → HCID 178526045, compound

Participants

Reaction Steps

(4-Cyanobenzylthio)acetic acid (from Example 3; 207 mg, 1 mmol) was added to a stirred solution of trimethylsilylazide (400 μL, 3 mmol) and dibutyltin oxide (25 mg, 100 μmol) in toluene (0.5 mL) at 110° C. After 6 hours, the reaction was quenched with MeOH (1 mL) and evaporated. The residue was purified by flash chromatography (silica gel; 1000:100:3 to 1000:100:13 CHCl3 /MeOH/HOAc) to give the title compound. Rf (silica; 1000:100:6 CHCl3 /MeOH/HOAc)=0.2 compared to the nitrile starting material of Rf =0.67. 1H NMR (d6DMSO); δ3.15 (s, 2H), 3.88 (s, 2H), 7.51 (d, 2H, J=8.1 Hz), 7.99 (d, 2H, J=8.1 Hz). FAB mass spectrum m/z=251 (M+1).

Provenance & Evidence