Water → 2,3-Dihydrobenzo(b)thiophene
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[S:1]1(=O)(=O)[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C.Cl>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2[S:1]1(=O)(=O)[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C.Cl>[S:1]1[CH2:5][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2A suspension of 2,3-dihydro-benzo[b]thiophene 1,1-dioxide (5.06 g, 30.08 mmol) in diethyl ether (150 mL) was added to a suspension of lithium aluminum hydride (10.27 g, 270.27 mmol) in diethyl ether (150 mL) at 25° C. After this time it was heated to reflux for 4 h (caution: if heating is too rapid it can exotherm rapidly and cause loss of material through the reflux condenser). It was then cooled to 0° C. in an ice bath and water (50 mL) was added very slowly. The resulting material was dissolved in 4 M aqueous hydrochloric acid (1 L). The aqueous layer was then extracted with diethyl ether (3×200 mL). The organic layers were combined and dried over magnesium sulfate, filtered and concentrated in vacuo. The material was purified by passing it through a plug of silica gel using pentane as the solvent to afford 2,3-dihydro-benzo[b]thiophene (1.88 g, 46%) as a clear colorless oil.
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