Aluminium lithium hydride → (5-Amino-2-trifluoromethoxy-phenyl)-methanol
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[O:11][C:12]([F:15])([F:14])[F:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][C:12]([F:13])([F:14])[F:15])=[C:4]([CH2:3][OH:2])[CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Amino-2-trifluoromethoxybenzoic acid methyl ester (3.0 g, 12.8 mmol) was dissolved under nitrogen in THF (20 mL) in a three-necked flask equipped with a thermometer and a separatory funnel. With stirring and ice-cooling lithium aluminium hydride (1 M in THF, 15 mL) was added dropwise over 10 min. Stirring was continued at room temperature for 1 hour, and the reaction mixture was concentrated in vacuo. The residue was suspended in DCM (150 mL) and water (50 mL), and filtered through celite. The filtrate was partitioned between DCM and water. The combined organic phases were washed with water (2×20 mL), dried (magnesium sulphate) and concentrated in vacuo to give 2.47 g of (5-amino-2-trifluoromethoxy-phenyl)methanol