tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide in dichloromethane 0.25 h; Ambient temperature;

1: 92 percent / H2SO4 / benzene; CH2Cl2 / 2.5 h / Heating 2: 99.3 percent / N-methylmorpholine N-oxide, (nC3H7)4NRuO4 / CH2Cl2 / 0.25 h / Ambient temperature View Scheme

1: NaBH4 / tetrahydrofuran; methanol / -10 °C 2: 1.) (EtO)3CH, pTsOH, 2.) pyridinium chlorochromate / 2.) CH2Cl2 View Scheme

toluene-4-sulfonic acid; orthoformic acid triethyl ester; pyridinium chlorochromate 2.) CH2Cl2; Yield given. Multistep reaction;

1.1: tetrahydrofuran / 0 °C 2.1: 1,1,1,3,3,3-hexafluoro-2-propanone; dihydrogen peroxide; disodium hydrogen phosphate dodecahydrate / water; dichloromethane / |Inert atmosphere 3.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / |Inert atmosphere 3.2: 1 h / 0 °C / |Inert atmosphere 4.1: triethylamine; acetic acid / |Inert atmosphere 5.1: sodium methylate / methanol 6.1: |Acidic conditions 7.1: perchloric acid / -10 °C / |Inert atmosphere 7.2: 2 h / -30 - -20 °C / |Inert atmosphere View Scheme

1: 98 percent / NaBH4 / methanol / 0.25 h / Ambient temperature 2: 23 mg / 70percent HClO4 / acetic acid / 0.17 h / ice-bath to room temperature View Scheme

1.1: tetrahydrofuran / 0 °C 2.1: 1,1,1,3,3,3-hexafluoro-2-propanone; dihydrogen peroxide; disodium hydrogen phosphate dodecahydrate / water; dichloromethane / |Inert atmosphere 3.1: magnesium; iodine / tetrahydrofuran / 20 - 50 °C / |Inert atmosphere 3.2: 1 h / 0 °C / |Inert atmosphere 4.1: triethylamine; acetic acid / |Inert atmosphere 5.1: sodium methylate / methanol 6.1: |Acidic conditions View Scheme

1: 85 percent / tetrahydrofuran 2: 35 percent / m-CPBA / CH2Cl2 View Scheme