Tetrahydrofuran → 2-(2-(O-tolylamino)benzo[d]oxazol-6-yl)acetic acid

Reaction equation

C1COCC1.[OH-].[Na+].[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([CH2:25][C:26]([O:28]C)=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1>Cl>[CH3:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]1[O:17][C:18]2[CH:24]=[C:23]([CH2:25][C:26]([OH:28])=[O:27])[CH:22]=[CH:21][C:19]=2[N:20]=1

Participants

Procedure

THF (30 ml) and 0.25N NaOH (32 ml, 8.00 mmol) were added to methyl 2-(2-methylphenylamino)-6-benzoxazolylacetate (1.18 g, 3.98 mmol), followed by stirring at room temperature for 5 hours. The reaction mixture was poured in 1N HCl (50 ml), followed by extraction with a chloroform-methanol (5:1, 2×200 ml) mixture. The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (867 mg, 77%) was obtained as a pale yellow amorphous substance.