1: conc. H2SO4 / Heating 2: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 3: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h View Scheme

1: pyridinium chlorochromate (PCC), sodium acetate / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h View Scheme

potassium tert-butylate 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h; Multistep reaction;

1: aq. KOH / ethanol / 1 h / Heating 2: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 3: diethyl ether / 72 h / Ambient temperature 4: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

potassium hydroxide in ethanol 1 h; Heating;