1: 69 percent / LDA / tetrahydrofuran / -78 - 20 °C 2: 77 percent / NaBH4; NaOH / methanol; H2O / 13 h / Heating View Scheme

cesium fluoride in water; N,N-dimethyl-formamide Heating;

1.1: sec-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: 79 percent / tetrahydrofuran; cyclohexane / -78 - 20 °C 2.1: 90 percent / CsF / dimethylformamide; H2O / Heating View Scheme

1: N,N-(diethyl)-3-methoxybenzene-1-carboxamide With N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium in tetrahydrofuran T=-78°C; 2: dimethyl-disulfide in tetrahydrofuran

1: 1.) s-BuLi, TMEDA / 1.) cyclohexane, THF, -78 deg C, 1 h, 2.) THF, cyclohexane, from -78 deg C to RT, 8 h 2: 1.) s-BuLi, TMEDA / 1.) cyclohexane, THF, -78 deg C, 1 h, 2.) THF, cyclohexane, from -78 deg C to RT, 8 h 3: 82 percent / CsF / dimethylformamide; H2O / 8 h / Heating View Scheme