potassium hydroxide in methanol Heating;

1: LDA / tetrahydrofuran / -78 °C 2: KOH / methanol / Heating View Scheme

1.1: sodium hydrogencarbonate / tetrahydrofuran / 0.17 h / 0 - 20 °C 1.2: 14 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 1.25 h / -75 - -35 °C / Inert atmosphere 2.2: 12 h / -75 - 20 °C / Inert atmosphere 3.1: potassium hydroxide; ethanol / 16 h / Reflux View Scheme

1.1: sodium hydrogencarbonate / tetrahydrofuran / 0.17 h / 0 - 20 °C 1.2: 14 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 1.25 h / -75 - -35 °C / Inert atmosphere 2.2: 12 h / -75 - 20 °C / Inert atmosphere 3.1: potassium hydroxide; ethanol / 16 h / Reflux View Scheme

1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 1.25 h / -75 - -35 °C / Inert atmosphere 1.2: 12 h / -75 - 20 °C / Inert atmosphere 2.1: potassium hydroxide; ethanol / 16 h / Reflux View Scheme

1: With trifluoroacetic acid in dichloromethane T=20°C; 6 h; 2: With sodium hydrogencarbonate in dichloromethane

1: NMM / tetrahydrofuran / 1 h / -15 °C 2: aq. NaN3 / tetrahydrofuran / -15 - 20 °C 3: toluene / 1.5 h / 90 °C 4: aq. KOH / tetrahydrofuran / 0 °C View Scheme