4,5,6,7-Tetrahydro-1-benzothiophene-3-carboxylic acid → 4,5,6,7-Tetrahydro-1-benzothien-3-ylmethanol
Reaction equation
[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([C:10](O)=[O:11])=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[S:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[C:3]([CH2:10][OH:11])=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylic acid (400 mg, 2.2 mmol) in diethyl ether (10 mL) was added under nitrogen to lithium aluminium hydride (1M solution in tetrahydrofuran, 3 mL, 3 mmol) in diethyl ether (10 mL) dropwise over 5 minutes. The reaction was stirred at room temperature for 1.5 hours then quenched with saturated ammonium chloride solution. The products were extracted into diethyl ether (x3). The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give 4,5,6,7-tetrahydro-1-benzothien-3-ylmethanol (320 mg, 86%). 1H NMR (500 MHz, CDCl3) δ 6.99 (1H, s), 4.56 (2H, s), 2.76 (2H, t, J=5.5 Hz), 2.58 (2H, t, J=5.6 Hz), 1.86–1.79 (4H, m), 1.43 (1H, s).