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

Temperature

50 °C

To a solution of 1-heptyne (2.62 mL, 1.91 g, d=0.7328, 20.0 mmol) in n-hexane (7 mL) was added a solution of DIBAL-H (20 mL, 1.0 M in n-hexane, 20.0 mmol 1.0 equiv) at −78° C. The reaction mixture was heated at 50° C. for 2 h, then was cooled to 0° C. 1-Chloro-1-methylsilacyclobutane (2.41 g, 20.0 mmol, 1.0 equiv) was added dropwise with syringe to the reaction mixture at 0° C., which was stirred for 48 h at 50° C. Cold water (1.28 mL, 71 mmol, 3.5 equiv) was added to the action solution carefully at 0° C. The resulting white suspension was filtered through Celite and the filtrate was concentrated in vacuo. The crude product was purified by column chromatography (SiO2, pentane) and distillation to afford 2.96 g (81%) of (E)-1 as a colorless oil. 1-Methyl-(1-heptynyl)silacyclobutane (145 mg, 8%) was also isolated after column chromatography.

1. temperaturewas cooled to 0° C
2. filtrationThe resulting white suspension was filtered through Celite
3. concentrationthe filtrate was concentrated in vacuo
4. distillationThe crude product was purified by column chromatography (SiO2, pentane) and distillation
5. customto afford 2.96 g (81%) of (E)-1 as a colorless oil

ORD record

ord-362c2a1f95d24800bc33ddabeaa627af

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06867323B2