[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:9][CH:10]([CH3:13])[CH2:11]Cl.[C:14](=O)([O-])[O-].[K+].[K+].[Cl-].[C-]#N.[K+].C1OCCOCCOCCOCCOCCOC1>CC(C)=O.C(#N)C>[CH3:13][CH:10]1[CH2:9][CH2:14][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[S:7][CH2:11]1Thiophenol was alkylated with 1-bromo-3-chloro-2-methylpropane in the presence of potassium carbonate (K2CO3) in acetone. The resulting primary chloride was lengthened by one carbon atom using KCN/18-crown-6 in acetonitrile. Basic hydrolysis, ring closure with polyphosphoric acid in analogy to Example 17(C) and Wolf-Kishner reduction according to Example 17(D) finally gave the required 2,3,4,5-tetrahydro-3-methyl-1-benzothiepine as a colorless oil.
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