反応 #70822
ord-9b74e036973a41e4be89156d2b6cabaf
反応方程式
反応条件
後処理
- 1workup.ADDITIONUpon completion of addition
- 2workup.STIRRINGUpon completion of the transfer, the reaction was stirred for 45 minutes
- 3その他quenched with saturated ammonium chloride solution
- 4その他to come to room temperature
- 5その他the aqueous and organic layers were separated
- 6抽出The aqueous phase was extracted 3× with ethyl acetate
- 7洗浄the combined organic phases were washed with brine
- 8乾燥dried over sodium sulfate
- 9濃縮concentrated in vacuo
- 10その他to yield a residue
- 11その他The residue was purified over silica gel
- 12洗浄eluting with 1%
実験手順
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.