Ethynyltributyltin → 3-[4-(tributylstannanyl)-1H-1,2,3-triazol-1-yl]propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A solution of tributylstannylethyne (1.47 g, 4.67 mmol) and 3-azidopropan-1-ol (450 mg, 4.4 mmol) in PhMe (15 mL) was heated at 80° C. under nitrogen for 3 days. Another 0.5 eq. of Tributylstannylethyne was added, and the resulting mixture was heated at 110° C. for 5 h. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (ISCO system: acetone/heptane=0-30%) to give the desired product as a colorless oil, 1.42 g, 77% yield. 1H NMR (CDCl3, 400 MHz): δ=7.48 (s, 1H), 4.57 (d, J=6.6 Hz, 2H), 3.63-3.67 (m, 2H), 2.11-2.17 (m, 2H), 1.95 (br s, 1H), 1.54-1.58 (m, 6H), 1.33-1.37 (m, 6H), 1.10-1.14 (m, 6H), 0.89 (t, J=7.3 Hz, 9H).

Provenance & Evidence