HCID 19389990, compound → HCID 19390052, compound

Participants

Reaction Steps

Butyllithium (0.92 ml; 1.6M solution in hexane) was added to a suspension of 0.217 g of (3-picolyl)triphenylphosphonium chloride hydrochloride monohydrate (Baker B. R. et al. J. Med. Chem. 1971, 14, 797) in 5 ml of anhydrous tetrahydrofuran, at 0° C. under nitrogen atmosphere. The yellow-orange mixture was stirred at room temperature for 0.5 hrs, then a solution of 0.05 g of 9-tert-butyldimethylsilyloxy-3-formyl-spiro[5.5]undecane (V, Prep. 8) in 1 ml of anhydrous tetrahydrofuran was added and the mixture was stirred at room temperature overnight. The reaction was quenched with a saturated aqueous solution of ammonium chloride. The layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The crude residue was purified by flash chromatography (SiO2 ; n-hexane/diethylether 70/30) to give 0.020 g of (E)-9-tert-butyldimethylsilyloxy-3-(2-(3-pyridyl)vinyl)-spiro[5.5]undecane and 0.020 g of (Z)-9-tert-butyldimethylsilyloxy-3-(2 -(3-pyridyl)vinyl)-spiro[5.5]undecane as white amorphous solids.

Provenance & Evidence