1,3-Butadiene → Silacyclopent-3-ene, 1-methyl-1-phenyl-

In a 500 mL two neck rb flask equipped with a reflux condenser, a Teflon covered magnetic stirring bar and a rubber septum was placed active magnesium powder (9.6 g, 0.4 mol), methylphenyldichlorosilane (38.2 g, 0.2 mol) and THF (300 mL). The reflux condenser was connected to a refrigeration unit. Ethylene glycol cooled to -20° C. was circulated through the reflux condenser. 1,3-Butadiene (15.1 g, 0.28 mol) was condensed at -78° C. into a volumetric flask which was sealed with a rubber septum. The 1,3-butadiene was transferred into the reaction via a cannula. The reaction mixture was stirred at rt for 24 h. Ether (2×100 mL) was added. The organic solution was decanted from the magnesium chloride salts. These were transferred to a sintered glass funnel and were washed with ether (100 mL). The combined organic solution was washed with water (2×50 mL), dried over anhydrous magnesium sulfate, filtered and the volatile solvents removed by evaporation under reduced pressure. The residue was purified by distillation through a 10 cm vacuum jacketed Vigreux column. The expected compound, bp 105°-107° C., 5 mm Hg, 42% yield, was collected.

1. customcondensed at -78° C. into a volumetric flask which
2. customwas sealed with a rubber septum
3. customThe organic solution was decanted from the magnesium chloride salts
4. customThese were transferred to a sintered glass funnel
5. washwere washed with ether (100 mL)
6. washThe combined organic solution was washed with water (2×50 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe volatile solvents removed by evaporation under reduced pressure
10. distillationThe residue was purified by distillation through a 10 cm vacuum
11. customThe expected compound, bp 105°-107° C., 5 mm Hg, 42% yield, was collected

ORDレコード

ord-99fc08697f314745b8f23c8c934f2ef3

出典データセット

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05171792