Tributyltin Chloride → 1-Methyl-5-(tributylstannyl)-1H-pyrazole

HRID 216363

Reaktionsgleichung

C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.Cl[Sn:16]([CH2:25][CH2:26][CH2:27][CH3:28])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH3:9][N:10]1[C:14]([Sn:16]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:13][CH:12]=[N:11]1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Lithium diisopropylamide (1.5 M in cyclohexane) (9.7 mL, 14.6 mmol) was added to a −78° C. solution of 1-methylpyrazole (1 g, 12.2 mmol) in tetrahydrofuran (15 mL). After stirring at −78° C. for 15 min, chloro-tri-n-butylstannane (3.9 mL, 14.6 mmol) was added dropwise. The reaction mixture was allowed to warm to ambient temperature overnight. The reaction mixture was quenched with saturated aqueous ammonium chloride, diluted with water and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-100 ethyl acetate/hexane afforded 1-methyl-5-(tributylstannyl)-1H-pyrazole.

Aufarbeitung

temperatureto warm to ambient temperature overnight
customThe reaction mixture was quenched with saturated aqueous ammonium chloride
additiondiluted with water
extractionextracted with ethyl acetate
dry with materialThe combined organic extracts were dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-8314bb2997214012b96ae829d21c7b06
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193228B2

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