[N+:1]([C:4]1[S:5][CH:6]=[CH:7][CH:8]=1)([O-])=O.Cl.[Sn].CCO[CH:14](OCC)[CH2:15][CH:16](OCC)OCC.N.O>CCO.[Cl-].[Cl-].[Zn+2]>[S:5]1[C:4]2=[N:1][CH:14]=[CH:15][CH:16]=[C:8]2[CH:7]=[CH:6]1
To a vigorously stirred mixture of 2-nitrothiophene (J-1) (13 g, 0.1 mol) and concentrated hydrochloric acid (195 mL) was added tin (25 g) at 0° C. After most of the tin was dissolved, EtOH (70 mL) and anhydrous ZnCl2 (6 g) were added. The mixture was heated to 85° C., and then treated with malonaldehyde bis(diethyl acetal) (17.2 g, 0.078 mol) in EtOH (30 mL). The resulting reaction was maintained at 85° C. for 1 h, then poured onto ice (100 g), basified with NH3.H2O, and extracted with DCM (75 mL×3). The combined organic layers were concentrated and purified by chromatography on silica gel to give the title compound. MS (m/z): 135 (M)+.
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