1-Heptyne → 1-Methyl-(1-heptynyl)silacyclobutane

Participants

Reaction Steps

To a solution of 1-heptyne (1.31 mL, d=0.7238, 0.960 g, 10.0 mmol) in Et2O (10 mL) was added a solution of MeLi (9.43 mL, 1.06 M in Et2O, 1.0 equiv) at −78° C. After being stirred for 3 h, 1-chloro-1-methylsilacyclobutane (1.16 mL, 1.0 equiv) was added dropwise to the reaction solution at the same temperature, which was then stirred for another 5 h. The reaction mixture was quenched with H2O (10 mL) and then was extracted with pentane (3×25 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to afford the crude product, which was purified by column chromatography (SiO2, pentane) and Kugelrohr distillation to afford 1.66 g (92%) of 1-(1heptynyl)-1-methylsilacyclobutane as colorless oil

Provenance & Evidence