1: 94 percent / triethylamine, DMAPi / CH2Cl2 2: OsO4-NMO 3: KOH / ethanol / Heating View Scheme

1.1: diethyl ether / 6 h / 20 °C 2.1: O3 / CH2Cl2; methanol / 1 h / -78 °C 2.2: Me2S / CH2Cl2; methanol / 1 h / -78 - 20 °C 3.1: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C 4.1: 0.49 g / HCl / diethyl ether / 0.5 h / 20 °C View Scheme

1.1: tetrahydrofuran / 1 h / Reflux 2.1: N-bromosuccinmide / dichloromethane / 3 h / Reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.05 h / -60 °C 3.2: 0.25 h / -60 °C 4.1: lithium hexamethyldisilazane / tetrahydrofuran / -60 - 20 °C 5.1: water; acetic acid / tetrahydrofuran / 0.5 h / 50 °C 6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.58 h / -48 °C 6.2: -48 - 20 °C 6.3: 0.5 h / 20 °C View Scheme

potassium carbonate; copper(I) bromide in dimethyl sulfoxide T=120°C; 24 h;

1.1: diethyl ether / 6 h / 20 °C 2.1: O3 / CH2Cl2; methanol / 1 h / -78 °C 2.2: Me2S / CH2Cl2; methanol / 1 h / -78 - 20 °C 3.1: aq. NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1 h / 20 °C View Scheme

With  water; triphenylphosphine in  tetrahydrofuran T=20°C; 12 h;   

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1744500', constants.ctx, '0')">carbamic acid 1,1-dimethylethyl ester</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '2349612', constants.ctx, '0')">boron trifluoride diethyl etherate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '741857', constants.ctx, '0')">acetonitrile</a> <br />T=0 - 20&deg;C;&nbsp;1&nbsp;h;&nbsp;<br /> &nbsp;