Reaktion #70822
ord-9b74e036973a41e4be89156d2b6cabaf
Reaktionsgleichung
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1workup.ADDITIONUpon completion of addition
- 2workup.STIRRINGUpon completion of the transfer, the reaction was stirred for 45 minutes
- 3Sonstigequenched with saturated ammonium chloride solution
- 4Sonstigeto come to room temperature
- 5Sonstigethe aqueous and organic layers were separated
- 6ExtraktionThe aqueous phase was extracted 3× with ethyl acetate
- 7Waschenthe combined organic phases were washed with brine
- 8Trocknendried over sodium sulfate
- 9Einengenconcentrated in vacuo
- 10Sonstigeto yield a residue
- 11SonstigeThe residue was purified over silica gel
- 12Wascheneluting with 1%
Vorschrift
In a flame-dried three-neck flask, a solution of 2-(benzyloxymethyl)-2H-tetrazole (2.01 g, 10.57 mmol) and tetramethylethylenediamine (3.16 mL, 21.4 mmol) in diethyl ether (30 mL) was cooled to −78° C. Once at the prescribed temperature, the mixture was treated with the dropwise addition of n-butyllithium (1.6 M in hexanes, 7.3 mL, 11.62 mmol), which caused the color of the solution to turn dark red. Upon completion of addition, the mixture was stirred for 10 minutes, and then transferred via cannula to a solution of tributyltin chloride (2.9 mL, 10.57 mmol) in diethyl ether (20 mL) which had been pre-cooled to −78° C. Upon completion of the transfer, the reaction was stirred for 45 minutes, and then quenched with saturated ammonium chloride solution. The mixture was allowed to come to room temperature, and the aqueous and organic layers were separated. The aqueous phase was extracted 3× with ethyl acetate, and the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield a residue. The residue was purified over silica gel, eluting with 1% then 5% then 10% ethyl acetate/hexanes to yield 2-(benzyloxymethyl)-5-(tributylstannyl)-2H-tetrazole (3.0 g, 60% yield) as a colorless oil.