1: With tert.-butyl lithium in diethyl ether; pentane T=-78°C; 2 h; Inert atmosphere; 2: With methanol in diethyl ether; pentane T=-78°C; Inert atmosphere;

1: With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 2 h; Inert atmosphere; 2: With methanol-d1 in tetrahydrofuran; pentane T=-78 - 20°C; Inert atmosphere;

potassium permanganate; sodium carbonate

1: 200 - 230 °C 2: diluted aqueous NaOH 3: water; potassium permanganate; sodium carbonate View Scheme

1.1: 90 percent / 24 h / 180 °C 2.1: 95 percent / KOH / methanol / 10 h / Heating 3.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 4.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 4.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C View Scheme

1.1: 90 percent / 24 h / 180 °C 2.1: 95 percent / KOH / methanol / 10 h / Heating 3.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 4.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 4.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 5.1: Mg; iodine / diethyl ether 5.2: 88 percent / diethyl ether / 3 h / 20 °C 6.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 7.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 7.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 7.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 8.1: 90 percent / tetrahydrofuran / 2 h / sonication 9.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 10.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 11.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 12.1: 28 percent / propionic acid / 48 h / 180 °C 13.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 14.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 15.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 16.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 17.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4267587', constants.ctx, '0')">potassium carbonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '635680', constants.ctx, '0')">acetone</a> <br />12&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: aqueous HCl; toluene; amalgamated zinc<br />2: aqueous NaOH; acetone<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 80 percent / zinc amalgam; HCl / ethanol / 3 h / Heating<br />2: 95 percent / K₂CO₃ / acetone / 6 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 92 percent / K₂CO₃ / acetone / 8 h / Heating<br /> <br /> &nbsp;