jones reagent in acetone T=0°C;

1: 86 percent / 70percent HF / CH2Cl2; pyridine / 1.) 0 deg C, 1 h, 2.) room temp., 1 h 2: 74 percent / NaBH4 / propan-2-ol; H2O / 1 h / 0 °C 3: 59 percent / Jones reagent / acetone / 0 °C View Scheme

1: 74 percent / NaBH4 / propan-2-ol; H2O / 1 h / 0 °C 2: 59 percent / Jones reagent / acetone / 0 °C View Scheme

1: 70 percent / t-BuOK / 2-methyl-propan-2-ol / Ambient temperature 2: 86 percent / 70percent HF / CH2Cl2; pyridine / 1.) 0 deg C, 1 h, 2.) room temp., 1 h 3: 74 percent / NaBH4 / propan-2-ol; H2O / 1 h / 0 °C 4: 59 percent / Jones reagent / acetone / 0 °C View Scheme

sodium hydroxide in diethyl ether 1 h; Yield given;

1: Py*(HF)x / CH2Cl2 / 72 h / 25 °C 2: 1N aq. NaOH / diethyl ether / 1 h View Scheme