Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoate → 6-(p-Chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal

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Reaction Steps

A solution of 3.5 g (7.7 mmol) of ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanoate (example 2) in 105 mL methylene chloride is cooled to -78° and to it is added slowly 15.2 mL (23.6 mmol) of 1.53M solution of diisobutylaluminum hydride in toluene. The solution is stirred at -78° for 10 minutes and then quenched by slow addition of 10.8 mL methanol. The solution is then allowed to warm to 0° by the removal of the cold bath, and then 350 mL of ether is added followed by 10.8 mL of saturated brine and 7.7 g finely powdered anhydrous sodium sulfate. The cloudy suspension is stirred vigorously at room temperature overnight. The salts are filtered off and washed with methylene chloride (10×20 mL). The filtrate is evaporated to give 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]hexanal.

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