Reaktion #303545

Reaktionsgleichung

Lithium diisopropylamide

1-methylpyrazole

chloro-tri-n-butylstannane

→

1-methyl-5-(tributylstannyl)-1H-pyrazole

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to ambient temperature overnight
2. 2
   SonstigeThe reaction mixture was quenched with saturated aqueous ammonium chloride
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   TrocknenThe combined organic extracts were dried (magnesium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo

Vorschrift

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.

Quelle