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 then 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. Upon completion of addition, the mixture was stirred for 10 minutes, 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. The resulting reaction was stirred for 45 min, then quenched with a saturated ammonium chloride solution. The reaction 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 to yield a residue. 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. additionUpon completion of addition
2. customThe resulting reaction
3. stirringwas stirred for 45 min
4. customquenched with a saturated ammonium chloride solution
5. customto come to room temperature
6. customthe layers were separated
7. extractionThe aqueous phase was extracted 3× with ethyl acetate
8. washthe combined organic phases were washed with brine
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated in vacuo
11. customto yield a residue
12. customThe residue was purified over silica gel
13. washeluting with 1%

ORD record

ord-993306437d2b4ee49815ad9e8811ef85

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501782B2