sodium ethanolate in ethanol 24 h; Heating; Yield given;

1: 80 percent / Br2 / CHCl3 / 1 h 2: 91 percent / Ph3P, imidazole, I2 / CH2Cl2 / 1 h 3: 97 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 1h, 2.) -78 deg C, 1 h, -78 deg C to 0 deg C, 2 h 4: 80 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2 h, 2.) -78 deg C, 1h 5: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 6: NaOEt / ethanol / 24 h / Heating View Scheme

1: NaBH4, I2 / tetrahydrofuran / 16 h 2: 80 percent / Br2 / CHCl3 / 1 h 3: 91 percent / Ph3P, imidazole, I2 / CH2Cl2 / 1 h 4: 97 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 1h, 2.) -78 deg C, 1 h, -78 deg C to 0 deg C, 2 h 5: 80 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2 h, 2.) -78 deg C, 1h 6: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 7: NaOEt / ethanol / 24 h / Heating View Scheme

1: 91 percent / Ph3P, imidazole, I2 / CH2Cl2 / 1 h 2: 97 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 1h, 2.) -78 deg C, 1 h, -78 deg C to 0 deg C, 2 h 3: 80 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2 h, 2.) -78 deg C, 1h 4: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 5: NaOEt / ethanol / 24 h / Heating View Scheme

1: 97 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 1h, 2.) -78 deg C, 1 h, -78 deg C to 0 deg C, 2 h 2: 80 percent / LDA / tetrahydrofuran; various solvent(s) / 1.) -78 deg C, 2 h, 2.) -78 deg C, 1h 3: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 4: NaOEt / ethanol / 24 h / Heating View Scheme

1: 1.) t-BuLi, 2.) n-Bu4NH2PO4 / 1.) THF, -78 deg C, 1 h, 2.) H2O, reflux, 12 h 2: NaOEt / ethanol / 24 h / Heating View Scheme