silver; zinc in methanol 0.583333 h; Ambient temperature;

1: 70 percent / LDA / tetrahydrofuran / -78 - 20 °C 2: 97 percent / 2N HCl / tetrahydrofuran / 1 h / Ambient temperature 3: 84 percent / oxalyl chloride / CHCl3 / room temp., 30 min., then reflux 40 min. 4: 80 percent / Zn-Ag / methanol / 0.58 h / Ambient temperature View Scheme

1: 84 percent / oxalyl chloride / CHCl3 / room temp., 30 min., then reflux 40 min. 2: 80 percent / Zn-Ag / methanol / 0.58 h / Ambient temperature View Scheme

1: 87 percent / NaH / diethyl ether 2: 1.) LDA / 1.) HMPA, THF, -78 deg C to -20 deg C, 2.) -78 deg C, 30 min 3: KOAc, H2O / dioxane 4: MCPBA, / CH2Cl2 / -10 °C 5: CaCO3 / toluene / 0.25 h / Heating View Scheme

1: 1.) LDA / 1.) HMPA, THF, -78 deg C to -20 deg C, 2.) -78 deg C, 30 min 2: KOAc, H2O / dioxane 3: MCPBA, / CH2Cl2 / -10 °C 4: CaCO3 / toluene / 0.25 h / Heating View Scheme

1: KOAc, H2O / dioxane 2: MCPBA, / CH2Cl2 / -10 °C 3: CaCO3 / toluene / 0.25 h / Heating View Scheme

1: MCPBA, / CH2Cl2 / -10 °C 2: CaCO3 / toluene / 0.25 h / Heating View Scheme

sulfuric acid T=100°C; Product distribution;