[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19]CC)=[O:18].[Li+].[OH-].Cl>C1COCC1.CO.O.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([OH:19])=[O:18]
Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate (701 mg, 2.3 mmol) was dissolved in THF/MeOH (1:1, 40 mL) and a solution of LiOH (167 mg, 7.0 mmol) in H2O (10 mL) was added. The reaction was stirred for ˜16 h and the pH adjusted to ˜3 by the addition of 3N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated to give 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acid (636 mg, 99% yield) as a tan solid.
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