Lithium Hydroxide → 3-Chloro-4H-thieno[3,2-b]pyrrole-5-carboxylic acid
Reaction equation
Cl[C:2]1[S:9][C:8]2[CH:7]=[C:6]([C:10](N[C@@H]3CC4C(=CC=CC=4)[C@H]3NC=O)=[O:11])[NH:5][C:4]=2[C:3]=1[Cl:25].[OH-:26].[Li+]>CO>[C:10]([C:6]1[NH:5][C:4]2[C:3]([Cl:25])=[CH:2][S:9][C:8]=2[CH:7]=1)([OH:11])=[O:26]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Chloro-5-methoxycarbonyl-4H-thieno[3,2-b]pyrrole (Method 1; 0.61 g, 2.83 mmol) was taken up in MeOH (10 ml) and was heated under reflux. Aqueous lithium hydroxide (2.0 M, 3.0 ml, 6.0 mmol) was added portionwise over 45 minutes. The mixture was heated under reflux for 30 minutes before being cooled and concentrated. Water (20 ml) was added and the solution was neutralised using aqueous hydrochloric acid (2.0 M, 3.0 ml). The solution was extracted using EtOAc, and the combined organic layers were concentrated to afford the title compound as a yellow solid (0.57 g, 100%). NMR: 12.4 (1H, br), 7.4 (1H, s), 7.0 (1H, s); m/z 200.3.