Multi-step reaction with 10 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 2.5 h / 1810.02 Torr
2: pyridine / 18 h / Ambient temperature
3: 86 percent / <(Ph3P)3P>4Pd, K3PO4 / dioxane / 18 h / 85 °C
4: methanol. NaOMe / 1 h / Ambient temperature
5: pyridine / CH2Cl2 / 1 h / 0 °C
6: 1.) LiCl, PdCl
26H5)3>2 / 1.) DMF, RT, 15 min, 2.) DMF, RT, 12 h
7: 1.) 9-BBN, 2.) aq. H2O2 / 1.) THF, RT, 48 h, 2.) THF, from 0 deg C to RT, 2 h
8: CrO3, H2SO4 / acetone / 38 h / 0 °C
9: CH2Cl2 / 1 h / Ambient temperature
10: 4-(dimethylamino)pyridine / CH2Cl2 / 18 h / Ambient temperature
With
pyridine; chromium(VI) oxide; dmap; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium(0); sulfuric acid; hydrogen; dihydrogen peroxide; sodium methylate; lithium chloride;
palladium on activated charcoal;
In
1,4-dioxane; ethanol; dichloromethane; acetone;
DOI:10.1021/jm950699x