pyridine; acetic anhydride; palladium in methanol; dichloromethane; chloroform; ethyl acetate

lithium tert-pentoxide in methanol; n-heptane; N,N-dimethyl-formamide T=-4 - 20°C;

triethylamine in dichloromethane T=0 - 20°C;

1: 1) n-BuLi / 1) THF, -78 deg C, 2) -78 deg C -> room temperature View Scheme

1: sodium azide / N,N-dimethyl-formamide / 70 °C 2: triphenylphosphine / tetrahydrofuran; water / 50 °C 3: triethylamine / dichloromethane / 0 - 20 °C View Scheme

1: sodium hydrogencarbonate / water; acetone / 0 °C 2: n-butyllithium / tetrahydrofuran / -78 - 20 °C 3: triethylamine / dichloromethane 4: sodium azide / N,N-dimethyl-formamide / 70 °C 5: triphenylphosphine / tetrahydrofuran; water / 50 °C 6: triethylamine / dichloromethane / 0 - 20 °C View Scheme

1: 10 palladium on activated charcoal; hydrogen / tetrahydrofuran 2: sodium hydrogencarbonate / water; acetone / 0 °C 3: n-butyllithium / tetrahydrofuran / -78 - 20 °C 4: triethylamine / dichloromethane 5: sodium azide / N,N-dimethyl-formamide / 70 °C 6: triphenylphosphine / tetrahydrofuran; water / 50 °C 7: triethylamine / dichloromethane / 0 - 20 °C View Scheme

1: triethylamine / dichloromethane 2: sodium azide / N,N-dimethyl-formamide / 70 °C 3: triphenylphosphine / tetrahydrofuran; water / 50 °C 4: triethylamine / dichloromethane / 0 - 20 °C View Scheme

1: 1) LiBr, Bu3PO, 2) NaOMe / 1) xylene, heating, 2) MeOH View Scheme

Multistep reaction;