[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O.[H-].[Na+].Cl>O1CCCC1>[S:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.[S:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[CH:1]=[C:12]([C:13]([OH:15])=[O:14])[CH2:11][CH2:10]1Ethyl 4-(2-formylphenylthio)butyrate (537 mg) was dissolved in 6 ml of tetrahydrofuran and a suspension of 60% sodium hydride (102 mg) in 5 ml of tetrahydrofuran was dropped at room temperature. Stirring was conducted at room temperature for 1 hour. The mixture was stirred for 30 minutes under reflux. During cooling in ice, 4 ml of a 1N hydrochloric acid was added. Extraction with 10 ml of ethyl acetate was conducted. The organic layer was washed with 20 ml of water three times. The quantitative analysis by HPLC found 220 mg (Yield 44%) of ethyl 2,3-dihydro-1-benzothiepine-4-carboxylate and 28 mg (Yield 6.4%) of 2,3-dihydro-1-benzothiepine-4-carboxylic acid.
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