C([O:8][C:9]1[CH:30]=[CH:29][C:12]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([Cl:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.CSC.B(F)(F)F.CCOCC.O>C(Cl)Cl>[Cl:28][CH:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:30][CH:29]=2)=[CH:17][CH:18]=1)[C:24]([O:26][CH3:27])=[O:25]Methyl 3-(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenyl)-2-chloropropanoate (1.0 g, 2.4 mmol) and dimethyl sulfide (0.9 g, 14 mmol) was dissolved in 60 ml CH2Cl2. Boron trifluoride etherate (2.0 g, 14 mmol) was added droppwise to the stirred solution. The reaction mixture was stirred for two days at room temperature. Another equivalent (0.4 g, 2.87 mmol) boron trifluoride etherate was added and the stirring was continued overnight. Water was added. The phases were separated and the aqueous phase was extracted twice with CH2Cl2. The organic phases were pooled, washed (water, brine), dried (Na2SO4) and evaporated under reduced pressure. Further purification by preparative HPLC using a gradient of CH3CN/5% CH3CN-waterphase containing 0.1M NH4OAc gave 0.55 g of the desired product (yield 52%) as an oil.
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