1: 90 percent / SOCl2 / 24 h / 25 °C 2: CH2Cl2 / 2 h / 25 °C 3: SOCl2 / CH2Cl2 / 0.5 h / 25 °C 4: 1.) sec-butyllithium / 1.) ether, 0 deg C, 4 h; 2.) ether, -78 deg C, 15 min then to r.t. 5: 98 percent / diethyl ether / 0.25 h / 0 °C 6: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1: 68 percent / Jones reagent / acetone / 25 °C 2: 90 percent / SOCl2 / 24 h / 25 °C 3: CH2Cl2 / 2 h / 25 °C 4: SOCl2 / CH2Cl2 / 0.5 h / 25 °C 5: 1.) sec-butyllithium / 1.) ether, 0 deg C, 4 h; 2.) ether, -78 deg C, 15 min then to r.t. 6: 98 percent / diethyl ether / 0.25 h / 0 °C 7: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1: CH2Cl2 / 2 h / 25 °C 2: SOCl2 / CH2Cl2 / 0.5 h / 25 °C 3: 1.) sec-butyllithium / 1.) ether, 0 deg C, 4 h; 2.) ether, -78 deg C, 15 min then to r.t. 4: 98 percent / diethyl ether / 0.25 h / 0 °C 5: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1: 98 percent / diethyl ether / 0.25 h / 0 °C 2: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1: 1.) sec-butyllithium / 1.) ether, 0 deg C, 4 h; 2.) ether, -78 deg C, 15 min then to r.t. 2: 98 percent / diethyl ether / 0.25 h / 0 °C 3: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

1: SOCl2 / CH2Cl2 / 0.5 h / 25 °C 2: 1.) sec-butyllithium / 1.) ether, 0 deg C, 4 h; 2.) ether, -78 deg C, 15 min then to r.t. 3: 98 percent / diethyl ether / 0.25 h / 0 °C 4: 88 percent / 3M H2SO4 / tetrahydrofuran / 12 h / 25 °C View Scheme

in diethyl ether 18 h; Ambient temperature;

2.) acid hydrolysis;

oxygen 1.) THF, -22 deg C - 25 deg C, 3 h, 2.) CHCl3, 18 h; Multistep reaction;