Benzo[b]thiophene-3-acetic acid → 2-(Benzo[b]thiophen-3-yl)ethanol
Reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([CH2:10][C:11](O)=[O:12])=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[S:1]1[CH:2]=[C:3]([CH2:10][CH2:11][OH:12])[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-benzothienylacetic acid (5.2 mmol) in 10 mL of anhydrous THF was slowly added to a stirred solution of LAH (10.4 mmol) in 50 mL of THF at 0° C. The ice bath was removed and the solution was stirred overnight, while it was allowed to warm to room temperature. The reaction was quenched by addition of water, 10% aqueous NaOH. The mixture was filtered over Celite and the filtrate was concentrated to give 2-(benzo[b]thiophen-3-yl)ethanol, which was used for tosylation.