[S:1]1[CH2:5][C:4](=[O:6])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2.Br[CH2:12][CH2:13][C:14](OCC)=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].C(OC(C)C)(C)C>CC(C)=O>[S:1]1[CH:5]=[C:4]([O:6][CH2:12][CH2:13][CH2:14][OH:15])[C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]1=2A mixture of benzo[b]thiophen-3-one (30 g), ethyl 3-bromopropionate (73 g), potassium carbonate (55 g), potassium iodide (1.3 g) and acetone (600 ml) was refluxed for 18 h. Filtration and removal of solvent in vacuo a red oil which was dissolved in ether (200 ml) and dried over magnesium sulfate. The ether solution was added dropwise to a suspension of lithium aluminium hydride (5 g) in ether (100 ml) followed by reflux for 1 h. Usual work-up gave a viscous oil which was applied to a silica gel column (eluent: isopropyl ether) giving 3-(benzo[b]thiophen-3-yloxy)-1-propanol (0.54 g) as an oil.
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