potassium hydroxide in methanol 24 h; Heating;

1: 100 percent / 15 h / 140 °C 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: 100 percent / H2 / 10percent Pd/C / ethyl acetate 5: 78 percent / KOH / methanol / 24 h / Heating View Scheme

1: 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 2: diethyl ether 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate 4: 78 percent / KOH / methanol / 24 h / Heating View Scheme

1: 100 percent / H2 / 10percent Pd/C / ethyl acetate 2: 78 percent / KOH / methanol / 24 h / Heating View Scheme