S(Cl)(Cl)=O.[Cl:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:23]=[CH:22][C:13]([C:14]([NH:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])=O)=[CH:12][CH:11]=1.O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[Cl:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:23]=[CH:22][C:13]([C:14]2[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[N:16]=2)=[CH:12][CH:11]=1Thionyl chloride (1.55 g, 13.09 mmol, 1.1 equiv.) is added dropwise to 4-(3-chloropropoxy)-N-(2-hydroxy-1,1-dimethylethyl)benzamide ax53 (3.18 g, 11.9 mmol, 1 eq) in dry dichloromethane (100 ml), under a nitrogen atmosphere over 30 min. The solution is then stirred for 3 h. Water and potassium carbonate are finally added and the mixture is stirred until no more bubbles are formed (pH=10). The layers are separated and the dichloromethane layer is washed with brine, dried over sodium sulfate and evaporated under vacuum to give 3.18 g of 2-[4-(3-chloropropoxy)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole ax10.
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