Water → 1-Ethylcyclopropane-1-sulfonyl chloride
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[CH2:1]([C:3]1([S:6]([O-:9])(=O)=[O:7])[CH2:5][CH2:4]1)[CH3:2].[K+].S(Cl)([Cl:13])=O.O>C(Cl)Cl.CN(C=O)C>[CH2:1]([C:3]1([S:6]([Cl:13])(=[O:9])=[O:7])[CH2:5][CH2:4]1)[CH3:2][CH2:1]([C:3]1([S:6]([O-:9])(=O)=[O:7])[CH2:5][CH2:4]1)[CH3:2].[K+].S(Cl)([Cl:13])=O.O>C(Cl)Cl.CN(C=O)C>[CH2:1]([C:3]1([S:6]([Cl:13])(=[O:9])=[O:7])[CH2:5][CH2:4]1)[CH3:2]To a mixture of potassium 1-ethylcyclopropane-1-sulfonate (0.420 g, 2.23 mmol, Preparation #JJJ.1) in thionyl chloride (3.58 mL, 49.1 mmol) was added DMF (0.016 mL, 0.20 mmol). The reaction was heated at about 80° C. for about 16 h. The reaction was cooled to 0° C. before the slow addition of water (10 mL). The reaction mixture was diluted with DCM (20 mL). The layers were separated and the aqueous portion was extracted with DCM (3×10 mL). The combined organic layers were separated, dried over anhydrous MgSO4, filtered, and concd under reduced pressure to afford crude 1-ethylcyclopropane-1-sulfonyl chloride (0.52 g, 83% yield, 60% purity) as an orange oil: 1H NMR (400 MHz, DMSO) d 2.09 (q, J=7.4, 2H), 1.62-1.60 (m, 2H), 1.45-1.39 (m, 2H), 0.91 (t, J=7.5, 3H).
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