sodium hydroxide; CsCO3 in dimethyl sulfoxide T=125 - 130°C; 17 - 24 h;

potassium hydroxide in water; tert-butyl alcohol

ammonium hydroxide

1.1: NaH / dimethylsulfoxide / 0.5 h / 20 °C 1.2: 75 percent / dimethylsulfoxide / 1 h / 20 °C 2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 2.2: tetrakis(triphenylphosphine)palladium / tetrahydrofuran; toluene / 1 h / Heating 3.1: Pd(PPh3)4; t-BuOK / ethanol / 80 °C 4.1: 24.0 g / KOH / 2-methyl-propan-2-ol / 6 h / Heating View Scheme

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 1.2: tetrakis(triphenylphosphine)palladium / tetrahydrofuran; toluene / 1 h / Heating 2.1: Pd(PPh3)4; t-BuOK / ethanol / 80 °C 3.1: 24.0 g / KOH / 2-methyl-propan-2-ol / 6 h / Heating View Scheme

1.1: NaH / dimethylformamide / 0.5 h / 20 °C 1.2: 51 percent / dimethylformamide / 16 h / 100 °C 2.1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 3.1: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 4.1: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 5.1: 207 mg / aq. NH3 / 1 h View Scheme

1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 2: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 3: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 4: 207 mg / aq. NH3 / 1 h View Scheme

1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 2: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 3: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 4: 207 mg / aq. NH3 / 1 h View Scheme

1.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 - -70 °C 1.2: 21.5 g / hexane; tetrahydrofuran / 4.17 h / -78 - 20 °C 2.1: 17.9 g / HCl / 20 h / Heating 3.1: 12.2 g / aq. sodium periodate / methanol / 1 h / 0 °C 4.1: trifluoroacetic anhydride / 0.5 h / Heating 4.2: Et3N; MeOH 5.1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 6.1: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 7.1: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 8.1: 207 mg / aq. NH3 / 1 h View Scheme

1.1: 79 percent / aq. LiOH / methanol; tetrahydrofuran / 24 h / Heating 2.1: n-BuLi / hexane; tetrahydrofuran / 0.75 h / -78 - -70 °C 2.2: 21.5 g / hexane; tetrahydrofuran / 4.17 h / -78 - 20 °C 3.1: 17.9 g / HCl / 20 h / Heating 4.1: 12.2 g / aq. sodium periodate / methanol / 1 h / 0 °C 5.1: trifluoroacetic anhydride / 0.5 h / Heating 5.2: Et3N; MeOH 6.1: 0.90 g / Pd(PPh3)4; t-BuONa / Heating 7.1: 488 mg / aq. LiOH / methanol; tetrahydrofuran / 11 h / Heating 8.1: oxalyl chloride / CH2Cl2 / 0.83 h / 0 - 20 °C 9.1: 207 mg / aq. NH3 / 1 h View Scheme