water; lithium hydroxide hydrate in tetrahydrofuran

1: 1.) Mg / 1.) ether, 2.) ether, RT, 1 h 2: 65 percent / CrO3, 30percent H2SO4 / acetone / 1 h / 0 deg C, then RT, 1h 3: 85 percent / N.N'-dicyclohexylcarbodiimide / 1,2-dimethoxy-ethane / 0 deg C, then RT, 4h 4: 1.) H2 2.) N,N-diisopropylethylamine / 1.) 10percent Pd/C / 1.) DMF, AcOH, H2O, RT, 2.) DMF, 3 h, RT 5: 1.) H2 2.) N,N-diisopropylethylamine / 1.) 10percent Pd/C / 1.) DMF, AcOH, H2O, RT, 2.) DMF, 3 h, RT 6: 46 percent / SO3-pyridene complex / pyridine; dimethylformamide / Ambient temperature View Scheme