HY-Zeolite 7 h; Heating;

1: 97 percent / pyridine / 0 - 20 °C 2: 88 percent / 2,4,6-collidine; triethylsilyl trifluoromethanesulfonate / CH2Cl2 / 0.5 h / 0 °C View Scheme

sodium acetate

1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) NaN(SiCH3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, b) r.t., 15 h 3: 97 percent / H2 / 10percent Pd/C / ethyl acetate 4: 95 percent / NaOH / methanol / 20 h / Heating View Scheme

1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 3: diethyl ether 4: 100 percent / H2 / 10percent Pd/C / ethyl acetate 5: 78 percent / KOH / methanol / 24 h / Heating View Scheme

1: 87 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 1.) 1M NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) 0 deg C, 1 h, r.t., 15 h 3: diethyl ether 4: 97 percent / H2 / 10percent Pd/C / ethyl acetate 5: 90 percent / NaOMe / methanol / Ambient temperature 6: 80 percent / pyridinium chlorochromate / CH2Cl2 / warming with a H2O bath 7: 1.) NaN(SiMe3)2 / 1.) THF, a) r.t., 30 min., b) reflux, 1 h, 2.) THF, a) -20 deg C , 1 h, b) r.t., 15 h 8: TsOH / methanol 9: 93 percent / NaOH / methanol / 27 h / Heating View Scheme