Multi-step reaction with 11 steps
1.1: tert.-butylnitrite / chloroform / 0.5 h / Darkness
1.2: 0.33 h / 20 °C / Irradiation; Inert atmosphere
2.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 0.17 h
2.2: 24 h / 40 °C
3.1: tributylphosphine / tetrahydrofuran / 3 h / 66 °C
4.1: dihydrogen peroxide / tetrahydrofuran; water / 4 h / 66 °C
5.1: potassium dioxotetrahydroxoosmate(VI); 4-methylmorpholine N-oxide / tetrahydrofuran; water; acetone; tert-butyl alcohol / 40 h / 23 °C
6.1: sodium periodate / tetrahydrofuran; water / 4 h / Reflux
7.1: toluene-4-sulfonic acid / water; benzene / 16 h / Reflux; Dean-Stark
8.1: W2-Raney nickel / ethanol / 3.5 h / 100 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 h / 66 °C
10.1: sodium nitrite / dichloromethane; acetic acid / 2 h / 23 °C
11.1: trifluoroacetic acid; triethylsilane / dichloromethane / 2 h / -20 °C
With
triethylsilane; sodium periodate; lithium aluminium tetrahydride; tert.-butylnitrite; potassium dioxotetrahydroxoosmate(VI); tributylphosphine; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; sodium nitrite;
In
tetrahydrofuran; ethanol; dichloromethane; chloroform; water; acetic acid; acetone; tert-butyl alcohol; benzene;
1.1: |Barton Nitrite Photolysis / 1.2: |Barton Nitrite Photolysis;
DOI:10.1002/chem.201502148