Tetrahydrofuran → Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-

HRID 495300

Reaktionsgleichung

Reaktionsgleichung von HRID 495300
O1CCCC1.[O:6]1[CH2:10][CH2:9][O:8][CH:7]1[C:11]1[O:12][CH:13]=[CH:14][CH:15]=1.C([Li])CCC.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>O.CCCCCC>[CH2:30]([Sn:25]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:26][CH2:27][CH2:28][CH3:29])[C:13]1[O:12][C:11]([CH:7]2[O:8][CH2:9][CH2:10][O:6]2)=[CH:15][CH:14]=1)[CH2:31][CH2:32][CH3:33]

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 2631582-Furyl-1,3-dioxolaneHCID 178418339Butyllithium

Produkt 1

HCID 10960952Stannane, tributyl[5-(1,3-dioxolan-2-yl)-2-furanyl]-Ausbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Tetrahydrofuran (10 mL) solution of 2-(1,3-dioxolan-2-yl)furan (1.0 g, 7.1 mmol) was cooled to −78° C., and n-hexane solution of 1.6 mol/L n-butyllithium (4.5 mL, 7.2 mmol) was dropwise added thereto, and stirred for 3 hours. Tributyltin chloride (2.6 g, 7.9 mmol) was dropwise added to the reaction mixture, and stirred for 5 hours with heating up to room temperature. Water (10 mL) was added to the reaction mixture, and extracted with ethyl acetate (50 mL). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20) to obtain tributyl[5-(1,3-dioxolan-2-yl)furan-2-yl]tin (2.3 g, 75%).

Aufarbeitung

  1. stirringstirred for 5 hours
  2. extractionextracted with ethyl acetate (50 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (n-hexane to ethyl acetate/n-hexane=1/20)

Quellen und Nachweise

ORD-Eintrag
ord-92705236b5794a5bb01450d143a7c481
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538241B2

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