CN(C=O)C.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH:15]([CH:19]([CH3:21])[CH3:20])[C:16]([OH:18])=[O:17])=[CH:12][C:11]=2[CH:22]=1.C([O-])([O-])=O.[K+].[K+].[O:29]([C:36]1[CH:37]=[C:38]([CH:41]=[CH:42][CH:43]=1)[CH2:39]Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCOCC>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[S:14][C:13]([CH:15]([CH:19]([CH3:20])[CH3:21])[C:16]([O:18][CH2:39][C:38]3[CH:41]=[CH:42][CH:43]=[C:36]([O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:37]=3)=[O:17])=[CH:12][C:11]=2[CH:22]=1A mixture of 20 ml DMF, 2-(5-chloro-2-benzothienyl)-3-methylbutanoic acid (0.5 g), K2CO3 (0.51 g) and 3-phenoxybenzyl bromide (0.44 g) is stirred, under nitrogen, for about 15 hours. The mixture is then taken up in ether, washed with water and brine, dried over Na2SO4 and solvent removed. The crude product is plated developing with 10% ether/hexane to give 3-phenoxybenzyl 2-(5-chloro-2-benzothienyl)-3-methylbutanoate.
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