S(Cl)([Cl:3])=O.C(N(CC)C1C=CC=CC=1)C.[CH3:16][S:17]([C:20]1[CH:21]=[C:22]([CH:26](O)[CH3:27])[CH:23]=[CH:24][CH:25]=1)(=[O:19])=[O:18].CCOC(C)=O>C1(C)C=CC=CC=1>[Cl:3][CH:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([S:17]([CH3:16])(=[O:19])=[O:18])[CH:21]=1)[CH3:27]Thionyl chloride (0.11 g, 0.91 mmol) was added to a solution of N,N-diethylaniline (0.19 g, 1.3 mmol) and 1-[3-(methylsulfonyl)phenyl]ethanol (0.26 g, 1.3 mmol) in toluene (4 mL) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes followed by addition of EtOAc. The organic phase was washed subsequently with 2M HCl (aq), water, saturated sodium bicarbonate, and brine, and then dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash column chromatography on silica (ethyl acetate:hexane gradient elution 20:80 to 25:75) to give the title compound (60 mg) that was used in the next step without any further purification (approximate purity 75%).
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