Tetrahydrofuran → 1-n-Butylmethylphenylsilyl-2,3,4,5-tetramethylcyclopentadiene

HRID 1261556Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261556
[CH3:1][C:2]1[CH2:6][C:5]([CH3:7])=[C:4]([CH3:8])[C:3]=1[CH3:9].Cl[Si:11](CCCC)(C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])O.[Na+].[C:28](=O)([O-])[O-].[Na+].[Na+].O1[CH2:38][CH2:37][CH2:36][CH2:35]1>C1(C)C=CC=CC=1>[CH2:35]([CH2:9][C:3]1[C:2]([SiH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH3:1])[C:6]([CH3:28])=[C:5]([CH3:7])[C:4]=1[CH3:8])[CH2:36][CH2:37][CH3:38]

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 1381631,2,3,4-TetramethylcyclopentadieneHCID 516892Sodium BicarbonateHCID 15628309HCID 15628309, Verbindung

Produkt 1

HCID 1317306631-n-Butylmethylphenylsilyl-2,3,4,5-tetramethylcyclopentadieneAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

After sodium hydride dispersed in mineral oil (0.80 g, 33.47 mmol as sodium hydride) was washed with hexane to remove the mineral oil under nitrogen atmosphere, tetrahydrofuran (38 mL) was added. The temperature of the mixture was elevated to 50° C. and aniline (0.21 g, 2.23 mmol) was added. The mixture was stirred at 50° C. for 1 hour. To the resultant mixture, a solution obtained by dissolving 1,2,3,4-tetramethylcyclopenta-1,3-diene (3.00 g, 24.55 mmol) in tetrahydrofuran (10 mL) was added dropwise and stirred at 50° C. for 2 hours. The solution was cooled to 0° C. To the solution, a solution obtained by dissolving chloro(n-butyl)methylphenyl silane (4.75 g, 22.32 mmol) in toluene (10 mL) was added dropwise and stirred at 35° C. for 2 hours. The resultant mixture was added dropwise to a mixed solution of a 10% sodium hydrogen carbonate solution (24 mL) and a 10% sodium carbonate solution (24 mL) at 0° C. Toluene (24 mL) was added to separate an organic phase. The organic phase was washed with water (40 nit) and further washed with a saturated brine (20 mL). The organic phase was dried over sodium sulfate and then filtrated. The solvent was concentrated under reduced pressure to obtain 1-n-butylmethylphenylsilyl-2,3,4,5-tetramethylcyclopentadiene (5.16 g, yield 77.4%).

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureThe solution was cooled to 0° C
  3. customTo the solution, a solution obtained
  4. additionwas added dropwise
  5. stirringstirred at 35° C. for 2 hours
  6. customat 0° C
  7. customto separate an organic phase
  8. washThe organic phase was washed with water (40 nit)
  9. washfurther washed with a saturated brine (20 mL)
  10. dry with materialThe organic phase was dried over sodium sulfate
  11. filtrationfiltrated
  12. concentrationThe solvent was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8afb58c31c904087a9cf073f32f3b318
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470947B2

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