Methanol → 5-Chloro-2-(2-chlorophenyl)-benzoxazole-7-propanoic Acid

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[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][CH2:20][OH:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1.C[OH:23].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]([OH:23])=[O:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])=[N:7][C:6]=2[CH:17]=1

참가 물질

실험 절차

10.3 ml (41 mmol of O) of Kiliani solution was added at −10° to −5° C. within 20 minutes to a solution of 6.44 g (20 mmol) of 5-chloro-2-(2-chlorophenyl)-7-(3-hydroxy-propyl)-benzoxazole in 130 mg of acetone. After 45 minutes, 5 ml of methanol and 130 ml of water were added. The acetone was removed in vacuo, the solid suspended, collected, and washed with 1 N sulfuric acid and water. The residue was taken up in 35 ml of 1 N NaOH and 50 ml of water, and extracted with ether. The water phase was acidified with 5 N HCl to pH 3. Filtration and washing gave the title compound (4.88 g, 72.6%), mp 152-4° C.