[C:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH:9]=O)(=[O:3])[CH3:2].Br[CH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[N:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[C:20]([C:18]1[N:19]=[C:15]([C:14]2[O:12][C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:11][C:8]=3[CH:9]=2)[S:16][CH:17]=1)([CH3:23])([CH3:22])[CH3:21]A mixture of 5-acetyl-2-hydroxybenzaldehyde (1.68 g), 2-bromomethyl-4-tert-butylthiazole, potassium carbonate (1.24 g) and potassium iodide (0.59 g) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 5 hours. The resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. A mixture of the resulting syrup and acetic anhydride in xylene was stirred under reflux for 1 day. After being cooled to room temperature, the reaction mixture was concentrated under reduced -pressure. The resulting syrup was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-(5-acetylbenzofuran-2-yl)thiazole (1.83 g).
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