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ChemicalBook CAS DataBase List Tributyl(5,6-dihydro-4H-pyran-2-yl)stannane
109669-45-6

Tributyl(5,6-dihydro-4H-pyran-2-yl)stannane synthesis

2synthesis methods
-

Yield:109669-45-6 59%

Reaction Conditions:

Stage #1: 3,4-dihydro-2H-pyranwith tert.-butyl lithium in tetrahydrofuran at -78 - 0; for 1 h;
Stage #2: tributyltin chloride in tetrahydrofuran at -78; for 0.25 h;

Steps:

6 Example 6

Example 6 2-Tributylstannyl-2,3-dihydropyran To a solution of 2,3-dihydropyran (2.0 g, 23.8 mmol) in dry THF (50 mL) was added tert-BuLi (25.2 mmol) at -78 °C and the resulting solution was stirred at 0 °C for 1 hour. The mixture was cooled to -78 °C and tributylstannyl chloride (5.53 g, 17.0 mmol) was added and stirring was continued for fifteen minutes at which time the reaction mixture was diluted with water and extracted 3x with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated. The crude product was filtered through a plug of silica gel to yield 5.23 g (59%) of the title compound as a clear liquid.

References:

EP944595,2003,B1 Location in patent:Page/Page column 14