Tributyltin Chloride → Hydrochloric Acid

Participants

Reaction Conditions

Reaction Steps

To neat tributyltin chloride (1250 μl, 4608 μmol) was added sodium azide (271 μl, 7691 μmol). After sting at 80° C. for 30 mins, to the mixture was added a solution of 23.E (178 mg, 437 μmol) in DMF. The resulting mixture was stirred at 160° C. under N2 for 1.5 hr, cooled and diluted with water. The resulting mixture was extracted with 30% iPrOH/CHCl3 (3×10 mL), and organic solvents was removed under reduced pressure. After purification of the residue by preparative HPLC (10-90% CH3CN/water, 30 min), the combined product fractions were treated with 1.0 N HCl (0.50 ml) and concentrated to provide 23.11 HCl salt colorless solid (121 mg, 57%) as. MS ESI (positve.) m/e: 451.1 (M+H), 1H NMR (400 MHz, CD3OD) δ ppm 7.82 (d, J=6.65 Hz, 1H), 7.23-7.45 (m, 4H), 7.11 (t, J=8.61 Hz, 2H), 6.88 (s, 1H), 4.71 (s, 2H), 4.60 (br. s., 1H) 3.63 (s, 3H) 3.42-3.54 (m, 1H), 3.20-3.29 (m, 1H), 3.01-3.11 (m, 4H).

Provenance & Evidence