Aluminium lithium hydride → (5-Chloro-1-benzothiophen-2-yl)methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([C:16](OC)=[O:17])=[CH:13][C:12]=2[CH:20]=1>CCOCC>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][C:14]([CH2:16][OH:17])=[CH:13][C:12]=2[CH:20]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To lithium aluminum hydride (26.5 mmol) and 50 ml ether, at -20° under nitrogen, is slowly added methyl 5-chlorobenzothiophene-2-carboxylate (6 g, 26.5 mmol). The mixture is then stirred at -20° for 10 minutes. After no starting material is detectable by thin layer chromatography, the mixture is quenched with 1 ml water, 1 ml 15% NaOH, and 3 ml water at -20°. The mixture is allowed to warm to RT and stirred for 15 hours. The mixture was then filtered and solvent evaporated to give 5-chlorobenzothiophene-2-methanol.