C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.[CH:14]1([CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15]1.[H-].[Na+]>CS(C)=O.C(OCC)C.[Cl-].[Na+].O>[CH:14]1([C:17]2[C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:10][NH:11][CH:12]=2)[CH2:16][CH2:15]1A solution of 8.77 g of p-toluenesulphonylmethyl isocyanide and 5.67 g of methyl 3-cyclopropylacrylate in 72 mL of dimethyl sulphoxide and 145 mL of diethyl ether is added dropwise over 1.5 hours and under an argon atmosphere to a suspension of 1.73 g (54 mmol) of sodium hydride (at 75% by weight in liquid petroleum jelly) in 90 mL of diethyl ether. The reaction is exothermic. After the reaction mixture has been stirred at room temperature for 2.75 hours, 180 mL of brine are added cautiously, and the mixture is extracted twice with 100 mL of diethyl ether. The organic phase is washed with water, dried and then concentrated to dryness under reduced pressure (2.7 kPa), giving 6.39 g of 4-cyclopropyl-3-methoxycarbonyl-1H-pyrrole in the form of a yellow solid melting at 107° C.
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