[K+].[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8](=[S:11])([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]([O:22][CH3:23])([O:20][CH3:21])[CH2:16][CH2:17][CH2:18]Br.C1OCCOCCOCCOCCOCCOC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8](=[S:11])([O:10][CH2:18][CH2:17][CH2:16][C:15]([O:22][CH3:23])([O:20][CH3:21])[O:14][CH3:13])=[O:9])=[CH:6][CH:7]=1A suspension of para-toluenethiosulphonic acid potassium salt (8.77 g), trimethyl 4-bromoorthobutyrate (8.00 g) and 18-crown-6 (10.24 g) in anhydrous tetrahydrofuran (60 ml) was ultrasonicated for 5 minutes then stirred at room temperature for 3 days. The mixture was poured into saturated aqueous sodium bicarbonate solution (200 ml) and extracted with ether (2×200 ml). The organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the subtitle compound (10.52 g) as an oil.
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