Sodium Hydroxide → 2-(2-Chloro-phenoxy)-4-(5-hydroxymethyl-imidazol-1-ylmethyl)-benzonitrile Hydrochloride
Reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][C:22]=1[C:23]#[N:24])[CH2:9][N:10]1[C:14]([CH2:15][O:16]C(=O)C)=[CH:13][N:12]=[CH:11]1.[OH-].[Na+]>C1COCC1>[ClH:2].[Cl:2][C:3]1[CH:28]=[CH:27][CH:26]=[CH:25][C:4]=1[O:5][C:6]1[CH:7]=[C:8]([CH2:9][N:10]2[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[CH:11]2)[CH:20]=[CH:21][C:22]=1[C:23]#[N:24]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of acetic acid 3-[3-(2-chloro-phenoxy)-4-cyano-benzyl]-3H-imidazol-4-ylmethyl ester hydrochloride (as described in Example 14)(0.112 g, 0.268 mmol) in THF (2.0 mL) was added 1M NaOH (0.536 mL). After 3.5 hr. the reaction was partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after conversion to the hydrochloride salt.