Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate

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Reaction Steps

To a solution of 3.08 g (7.5 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal in 40 mL chloroform is added 2.88 g (8.4 mmol) of methyl (triphenylphosphoranylidene)-acetate and then subjected to reflux for 3 hours. The solvent is evaporated and the residue taken up in ether and extracted with 0.5N HCl (3×20 mL). The aqueous extracts are combined and washed with ether. The aqueous phase is adjusted to pH 8 and then extracted with methylene chloride (3×50 mL). Combined organic extracts are dried (MgSO4), filtered and then evaporated to give an amber oil. This is purified by flash chromatography using 7:3 EtOAc: hexane as the eluent to give methyl 8-(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]-oct-2-enoate as an oil.

Provenance & Evidence