Cl[CH2:2][Cl:3].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]1[O:10][C:11]([CH3:16])=[C:12](CO)[N:13]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O>[Cl:3][CH2:2][C:12]1[N:13]=[C:9]([C:5]2[O:4][CH:8]=[CH:7][CH:6]=2)[O:10][C:11]=1[CH3:16]The dichloromethane (1 mL) solution of {2-(furan-2-yl)-5-methyloxazol-4-yl}methanol (36 mg, 0.2 mmol), N,N-dimethylaminopyridine (37 mg, 0.3 mmol) and p-toluene sulfonyl chloride (57 mg, 0.3 mmol) was stirred at 60° C. for 2 hrs. The reaction mixture was added water and extracted with ethyl acetate. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain 4-(chloromethyl)-2-(furan-2-yl)-5-methyloxazole (13 mg, 31%) as a transparent oil.
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