Water → 2-((Methoxymethyloxy)methyl)-6-(tributylstannyl)pyridine

Participants

Reaction Conditions

Reaction Steps

Under a stream of argon, compound (11) (24.7 g; 106 mmol) was dissolved in anhydrous tetrahydrofuran (270 mL), and 1.54M n-butyllithium hexane solution was added dropwise thereto over 50 minutes at −65 to −70° C. The resulting reaction mixture was stirred at −65 to −70° C. for 1 hour. To the reaction mixture, tetrahydrofuran solution of 40 g (122 mmol) of tributyltin chloride (100 mL) was added dropwise over 30 minutes. While gradually raising the temperature of the reaction solution (to −20° C.), the reaction mixture was stirred at −20° C. for 20 hours. To the reaction mixture, water (250 mL) was added, and the resulting mixture was extracted with diethyl ether three times. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to give 58 g of the crude title compound (12). The obtained compound was used in the next step without further purifying.

Provenance & Evidence