1: 89 percent / Jones reagent / acetone / 0 °C 2: 92 percent / diethyl ether / 0 °C 3: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C 4: 95 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 5: 44 percent / K2CO3; KI / dimethylformamide; toluene / 7 h / Heating 6: 67.6 percent / NaOH; MeOH / 2 h / Heating View Scheme

1: 89 percent / Jones reagent / acetone / 0 °C 2: 92 percent / diethyl ether / 0 °C 3: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C View Scheme

1: 89 percent / Jones reagent / acetone / 0 °C 2: 92 percent / diethyl ether / 0 °C 3: 89 percent / HCl; H2O / tetrahydrofuran / 15 h / 20 °C 4: 95 percent / NaBH4 / methanol; tetrahydrofuran / 0.5 h / 0 °C 5: 44 percent / K2CO3; KI / dimethylformamide; toluene / 7 h / Heating View Scheme