1: With potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; tetrakis(triphenylphosphine) palladium(0) in benzene P=34200 Torr; 16 h; Photolysis; 2: With tetrabutyl ammonium fluoride in tetrahydrofuran; chloroform T=20°C; 3 h;

1: 3-methoxy-4-hydroxybenzylamine hydrochloride With sodium hydrogencarbonate in water T=20°C; 0.5 h; 2: 8-methyl-nonanoyl chloride in chloroform; water T=20°C; 0.5 h;

hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 4 h;

hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 4 h;

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 4: aq. KOH / ethanol / 1 h / Heating 5: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 6: diethyl ether / 72 h / Ambient temperature 7: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

1: 1.) t-BuOK / 1.) DMF, RT, 5 min, 2.) a) RT, 20 h, b) 90 deg C, 1 h 2: aq. KOH / ethanol / 1 h / Heating 3: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 4: diethyl ether / 72 h / Ambient temperature 5: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr 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 3: aq. KOH / ethanol / 1 h / Heating 4: thionyl chloride / 1.) RT, 18 h, 2.) 100 deg C, 30 min 5: diethyl ether / 72 h / Ambient temperature 6: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme

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

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

1: diethyl ether / 72 h / Ambient temperature 2: H2 / 10percent Pd/C / ethanol / 4 h / 760 Torr View Scheme