C[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][CH:14]([CH3:19])[CH2:15][C:16](Cl)=[O:17].Cl[Sn](Cl)(Cl)Cl.O.Cl[CH2:27]Cl>>[CH3:13][CH:14]([CH3:19])[CH2:15][C:16]([C:4]1[S:3][CH:2]=[C:6]([C:7]2[CH:8]=[C:9]([CH3:27])[CH:10]=[CH:11][CH:12]=2)[CH:5]=1)=[O:17]A solution of 2-methyl-3-phenylthiophene (102.8 g, 0.590 mol) and 3-methylbutanoyl chloride (72.3 g, 0.600 mol) in 60 mL of dichloromethane was added dropwise to a 1 M solution of SnCl4 in dichloromethane (640 mL, 0.640 mol) at 0° C. The solution was stirred for 6 h at room temperature then poured slowly into water (500 mL). The organic fraction was separated, washed with a saturated aqueous solution of NaHCO3, brine solution, and dried (MgSO4). Solvents were removed on a rotoevaporator and the product was distilled (145° C., ˜0.03 torr). Yield=132.9 g. 1H-NMR δ (CDCl3): 7.61 (s, 1H), 7.3–7.5 (m, 5H), 2.72 (d, 2H), 2.52 (s, 3H), 2.3 (m, 1H), 1.0 (d, 6H). EIMS: m/z (%) 258 (M+, 38), 243 (25), 216 (69), 201 (100), 174 (11), 129 (25), 115 (11).
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