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Representative Procedure: Synthesis of 1-Benzyl-3, tert-butyldimethylsilyloxy)-2-methyl-1H-indole (4b) In an ACE pressure tube under an argon atmosphere the ligand 2,6-di-tert-butyl-4-methylphenol (22.0 mg, 0.1 mmol) is dissolved in 3 mL dry toluene. To this solution N-benzyl-N-phenylhydrazine (257.7 mg, 1.3 mmol, tert-butyldimethylsiloxy-2-propyne (209.0 mL, 1.0 mmol) and Ti(NEt2)4 (18 μL, 0.05 mmol) were added. The reaction mixture was heated at 100°C for 24 h. Then the pressure tube was opened under argon to add ZnCl2 (410.0 mg, 3.0 mmol, The reaction mixture was heated at 100°C for further 24 h. After cooling to r.t. the solution was decanted and the dark residue was washed with toluene and EtOAc. After removal of the combined solvents in vacuo and purification by column chromatography (eluent: hexane-EtOAc, 10:1) yielded 1-benzyl-3-tert- butyldimethylsilyloxy
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29NOSi: 351.2013; found: 351.1999.
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