N,N,N',N'-Tetramethylethylenediamine → 2-((Phenylmethoxy)methyl)-5-(tributylstannyl)-2H-tetrazole

Temperature

-78 °C

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. and treated with the dropwise addition of n-butyllithium (1.6 M in hexanes, 7.3 mL, 11.62 mmol), causing the color of the solution to turn dark red. The mixture was stirred for 10 minutes, then transferred via canulus 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. The reaction was stirred for 45 minutes, then quenched with saturated ammonium chloride solution. The mixture was allowed to come to room temperature, and the 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. The residue was purified over silica gel, eluting with 1% then 5% then 10% ethyl acetate/hexanes to yield the title compound (3.0 g, 60% yield) as a colorless oil.

1. stirringThe reaction was stirred for 45 minutes
2. customquenched with saturated ammonium chloride solution
3. customto come to room temperature
4. customthe layers were separated
5. extractionThe aqueous phase was extracted 3× with ethyl acetate
6. washthe combined organic phases were washed with brine
7. dry with materialdried over sodium sulfate
8. concentrationconcentrated in-vacuo
9. customThe residue was purified over silica gel
10. washeluting with 1%

ORD record

ord-d3a94fdbd36e4793af227d015fd00ea3

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985861B2