[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19]Cl.Cl>CN(C)C=O>[CH3:14][Si:15]([CH3:22])([CH3:21])[CH2:16][CH2:17][O:18][CH2:19][N:3]1[C:11]2[C:6](=[CH:7][C:8]([CH:12]=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4]1To a stirred suspension of 5.45, sodium hydride (55%) in mineral oil) in 100 ml N,N-dimethylformamide was added at 0-5° C. a solution of 16.8 g indole-5-carboxaldehyde in 100 ml N,N-dimethylformamide followed by 24.46 ml of 2-(trimethylsilyl)-ethoxymethyl chloride. The reaction mixture was then warmed up to ambient temperature and stirring continued for 16 hours. It was then poured onto ice, neutralized to pH 4 with HCl (1N) and extracted 3 times with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a brown oil, which was purified by chromatography (silicagel, eluent: gradient of n-heptane/EtOAc) to yield 25.52 g 1-(2-trimethylsilanyl-ethoxymethyl)-1H-indole-5-carbaldehyde as light yellow oil.
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