[Cl:1][C:2]1[C:3]([OH:15])=[C:4]([CH2:12][CH2:13][CH3:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:16]([O:18][C:19](=[O:41])[CH2:20][O:21][C:22]1[CH2:23][C:24]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]Br)(CCC)[C:25]([C:28](=[O:30])[CH3:29])=[CH:26][CH:27]=1)[CH3:17].C(=O)([O-])[O-].[K+].[K+].[CH3:48][C:49]([CH3:51])=O>CN(C)C=O>[CH2:16]([O:18][C:19](=[O:41])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][O:15][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]([OH:11])[C:4]=2[CH2:12][CH2:13][CH3:14])[C:23]=1[CH2:48][CH2:49][CH3:51])[CH3:17]A mixture of 1.10 g (0.0049 mole) of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone, 2.08 g (0.0049 mole) of [4-acetyl-3-[(5-bromopentyl)oxy]-3-propylphenoxy]acetic acid ethyl ester and 1.33 g (0.0097 mole) of potassium carbonate in 40 ml of anhydrous acetone and 20 ml of anhydrous dimethylformamide was stirred at reflux for 22 hours. The reaction mixture was concentrated in vacuo and the residue was purified by HPLC using 25% ethyl acetate-hexane to give 0.96 g (34% yield) of [4-acetyl-3-[5-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)pentyloxy]-2- propylphenoxy]acetic acid ethyl ester as an oil.
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