1: ethyl 2,4-dimethoxy-6-methylbenzoate With lithium diisopropyl amide in tetrahydrofuran; hexane T=-78°C; 0.333333 h; 2: 1-bromo-tetradecane in tetrahydrofuran; hexane T=-78 - 20°C;

1: H2, CH3COOH, CH3COONa / Pd/C / 760 Torr / Ambient temperature 2: 81 percent / K2CO3 / acetone / 12 h / Heating 3: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT View Scheme

1.1: 4.15 g / NaH2PO4; NaClO2 / dimethylsulfoxide; H2O / 20 °C 2.1: 99 percent / DBU / acetonitrile / 20 °C 3.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 3.2: 70 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1.1: 99 percent / DBU / acetonitrile / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: 70 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

1: 81 percent / K2CO3 / acetone / 12 h / Heating 2: 1.) n-butyllithium, diisopropylamine / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT View Scheme