1: C15H23ClO2 With 1-N,N-dimethylaminonaphthalene; lithium in tetrahydrofuran T=-65°C; 2 h; 2: methyl iodide in tetrahydrofuran T=-65 - 20°C; 3: With hydrogenchloride in tetrahydrofuran T=20°C; Further stages.;

bis(benzonitrile)palladium(II) dichloride; p-benozquinone in tetrahydrofuran Heating;

1.1: trimethyl orthoformate; p-toluenesulfonic acid hydrate; mol. sieves / CH2Cl2 / 15 h / 20 °C 2.1: Li; N,N-dimethyl-1-naphthylamine / tetrahydrofuran / 2 h / -65 °C 2.2: tetrahydrofuran / -65 - 20 °C 2.3: 88 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 h 2: K3PO4 / propan-2-ol / 32 h / Heating View Scheme

potassium phosphate in isopropyl alcohol 32 h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

lithium dimethyl cuprate 1) THF, -78 deg C; 2) HMPA, -78 deg C to r.t.; Yield given. Multistep reaction;

(i) LDA, (ii) aq. AcOH, (iii) KOH, EtOH; Multistep reaction;