Water → Ethyl 2-(1-azetidinylsulfinyl)-2-methylpropanoate

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Reaction Steps

Chlorine gas is bubbled through a biphasic mixture of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester (5.0 g, 26 mmol) in dichloromethane (50 mL) and water (50 mL) at 10° C. for 10 min. After this time, the organic phase is separated, dried (MgSO4), filtered and concentrated under reduced pressure. The crude sulfinyl chloride is re-dissolved in dichloromethane (50 mL) and N,N-diisopropylethylamine (4.58 mL, 26 mmol) and azetidine (1.5 g, 26 mmol) are introduced. The reaction is stirred at room temperature for 1 h and then concentrated under reduced pressure. Purification by chromatography on silica eluting with ethyl acetate/heptanes provides the title compound, m/z 220 [M+H+]

Provenance & Evidence