1: 53 percent / t-BuLi / diethyl ether 2: 70 percent / NaOEt / ethanol / -15 °C 3: 85 percent / CH2Cl2 / Ambient temperature 4: 85 percent / toluene / 12 h / 160 °C 5: 70 percent / HCOOH / Heating 6: 98 percent / LiOH / H2O; tetrahydrofuran / Ambient temperature 7: 98 percent / Ph2PON3, NEt3 8: 80 percent / HOAc / H2O View Scheme

1: 53 percent / t-BuLi / diethyl ether 2: 70 percent / NaOEt / ethanol / -15 °C 3: 85 percent / CH2Cl2 / Ambient temperature 4: 85 percent / toluene / 12 h / 160 °C 5: 70 percent / HCOOH / Heating 6: 98 percent / LiOH / H2O; tetrahydrofuran / Ambient temperature View Scheme

1: 1-(methoxymethyl)-1H-indole With n-butyllithium in tetrahydrofuran T=0°C; 2: triethyl borane in tetrahydrofuran T=0°C; 3: benzaldehyde With methanol in tetrahydrofuran T=0 - 20°C; 20 h;

1.1: pentane; tetrahydrofuran / 0.33 h / -30 °C 1.2: pentane; tetrahydrofuran; hexane / 1 h / -30 °C 2.1: 65 percent / MeOH / 2 h / 20 °C View Scheme

sodium hydroxide; n-butyllithium; dihydrogen peroxide multistep reaction, mechanism of intramolecular 1,2-alkyl migration; other trialkylboranes, also reactions with 1-methylindole;