boron trifluoride diethyl etherate in diethyl ether 0.166667 h;

1: 59 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, 4 Angstroem sieves / CH2Cl2 / 2 h / Ambient temperature 2: 94 percent / BF3*Et2O / diethyl ether / 0.17 h / Ambient temperature View Scheme

1: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -70 deg C, 20 min, 2.) CH2Cl2, overnight 2: NaBH3CN / acetonitrile; H2O; tetrahydrofuran / 1 h / Ambient temperature View Scheme