Dess-Martin periodane in dichloromethane T=20°C; 2.5 h;

in toluene T=60°C; 40 h;

camphor-10-sulfonic acid in tetrahydrofuran T=20°C; 3 h;

hydrogenchloride; sodium hydroxide; ammonium chloride in tetrahydrofuran; hexane; n-heptane; water; ethyl acetate; toluene

in toluene 12 h; Heating / reflux;

hydroxylamine hydrochloride; water in methanol; acetone T=55 - 65°C; 0.833333 - 1.25 h; Product distribution / selectivity;

phosphoric acid in acetonitrile T=80°C; 3 h;

2: 73.9 g / methanol; tetrahydrofuran / 0 °C 3: 73 g / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 4 h / -70 °C View Scheme

1: 43 percent / acetic anhydride / 4 h / 90 °C 2: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d 3: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h 4: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT 5: toluene / 6 h / Heating View Scheme

1: NaOH / methanol; H2O / 2 h / Heating 2: 43 percent / acetic anhydride / 4 h / 90 °C 3: 1.) concd. HCl, 2.) p-TSA, H2O / 1.) ethanol, reflux, 24 h, 2.) acetone, reflux, 2 d 4: 1.) sodium hydride, n-butyllithium / 1.) THF, hexane, 0 deg C, 30 min, 2.)a) -78 deg C, 30 min, b) 0 deg C, 1 h 5: 1.) tributylborane, sodium borohydride, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, a) RT, b) 0 deg C, 3 h, 2.) RT 6: toluene / 6 h / Heating View Scheme