1-Bromoheptane → 5-Benzyloxy-1-heptylindole

Reaction equation

[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[CH:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH:15]=[CH:14]2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Procedure

0.22 g (4.45 mmol) pulverized, 88% potassium hydroxide, 0.5 g (2.24 mmol) 5-benzyloxyindole and 0.07 g (0.22 mmol) tetrabutylammoniumbromide are weighed out in the given order and mixed with 1.41 ml (8.96 mmol) 1-bromoheptane with vigorous stirring. The mixture is stirred at room temperature overnight. Having added 30 ml water, three extractions using diethyl ether are carried out. The organic phase is washed three times with saturated NaCl solution, dried on sodium sulfate and the solvent is removed in vacuo. The residue is purified on silica gel by means of column chromatography (flow agent: hexane/ethyl acetate 95:5). The product accrues as an oil.