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

HRID 1681368

반응식

HRID 1681368 반응식
[Mg].[CH3:2][Si:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(Cl)Cl.[CH2:12]1[CH2:16]O[CH2:14][CH2:13]1.C=CC=C>CCOCC.C(O)(C)C>[CH3:2][Si:3]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:14][CH:13]=[CH:12][CH2:16]1

참가 물질

7

반응물 4

HCID 78451,3-Butadiene2회HCID 8028TetrahydrofuranHCID 9006DichloromethylphenylsilaneHCID 5462224Magnesium

생성물 1

HCID 570903Silacyclopent-3-ene, 1-methyl-1-phenyl-수율 65%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 3776Isopropanol용매

실험 절차

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 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. Isopropyl alcohol 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 (boiling point 85°-87° C. at 4 mm Hg, 22.6 g, 65 % yield) was collected.

후처리

  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

출처 및 근거

ORD 기록
ord-bbfde3e8f0be4c5d8fc08b4796587721
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05171810

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