Hexane → N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tributyl-stannyl)benzyl)-N-methylprop-2-en-1-amine

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Reaction Conditions

Reaction Steps

Compound 12 (470 mg, 945 μmol) was dissolved in freshly distilled THF (5 mL) under nitrogen atmosphere and cooled to −78° C. n-butyllithium 1.6M in hexane solution (886 μL, 1.42 mmol) was then added and the mixture stirred 30 min at −78° C. Tributyltin chloride (462 mg, 1.42 mmol) in solution in THF (2 mL) was added and the mixture let to warm to room temperature overnight. A 0.1M ammonium chloride solution (5 mL) was added to the reactionnal mixture. The organic layer was isolated and the aqueous layer was extracted with dichloromethane (2×5 mL). The organic layers were combined and dried over sodium sulfate. After solvent evaporation under reduced pressure, the residue was purified over silica gel with heptane/acetone (98/2) as eluant to give 524 mg (794 μmol, 84% yield) of a yellowish oil.

Provenance & Evidence