1: methanol; sodium methylate / 4 h / 20 °C 2: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 3: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 4: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 5: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 6: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: CuSO4‵5H2O; acetic acid; zinc / water / 2.5 h / 0 °C 2: methanol; sodium methylate / 4 h / 20 °C 3: dipyridinium dichromate; acetic acid / ethyl acetate / 16 h / 20 °C 4: caesium carbonate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5: Oxonereg;; C8H6O4(2-)*Cu(2+) / toluene / 6 h / 60 °C / Molecular sieve; Air atmosphere 6: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 7: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: 51 percent / phosphorus pentasulfide; sodium hydrogencarbonate / tetrahydrofuran / 3 h / 20 °C 2: 22 percent / sodium acetate; triphenylphosphine / 0.5 h / 140 °C View Scheme

1: 79 percent / triethylamine / CH2Cl2 / 0.17 h / 0 °C 2: 22 percent / sodium acetate; triphenylphosphine / 0.5 h / 140 °C View Scheme

1: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / tetrachloromethane 2: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

1: N-bromosuccinmide / tetrachloromethane / 0.25 h / Reflux 2: toluene-4-sulfonic acid / toluene / 1 h / Reflux View Scheme

N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane Reflux;

sodium acetate T=120°C; 3 h;

1.1: triethylamine / dichloromethane / 3 h / |Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 20 °C / |Inert atmosphere 3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / -10 °C / |Inert atmosphere 3.2: |Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C / |Inert atmosphere 5.1: pyridine / 3.17 h / 0 - 20 °C / |Inert atmosphere 6.1: triethylamine / dichloromethane / 1 h / 20 °C / |Inert atmosphere 7.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / |Inert atmosphere; |Reflux 8.1: trichlorophosphate / 2 h / 20 - 50 °C / |Inert atmosphere 9.1: tert-butylamine borane / dichloromethane / 0.33 h / 20 °C / |Inert atmosphere 9.2: 2 h / |Inert atmosphere; |Reflux View Scheme

1.1: Dess-Martin periodane / dichloromethane / 20 °C / |Inert atmosphere 2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / -10 °C / |Inert atmosphere 2.2: |Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C / |Inert atmosphere 4.1: pyridine / 3.17 h / 0 - 20 °C / |Inert atmosphere 5.1: triethylamine / dichloromethane / 1 h / 20 °C / |Inert atmosphere 6.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / |Inert atmosphere; |Reflux 7.1: trichlorophosphate / 2 h / 20 - 50 °C / |Inert atmosphere 8.1: tert-butylamine borane / dichloromethane / 0.33 h / 20 °C / |Inert atmosphere 8.2: 2 h / |Inert atmosphere; |Reflux View Scheme