1: ozone / CH2Cl2; pyridine / -78 °C 2: 260 mg / 0.5 percent HCl / methanol / 24 h / 5 °C 3: NaBH4 / acetic acid / 4 h / Ambient temperature View Scheme

1: ozone / CH2Cl2; pyridine / -78 °C 2: 260 mg / 0.5 percent HCl / methanol / 24 h / 5 °C 3: NaBH4 / acetic acid / 4 h / Ambient temperature 4: 86 percent / Jones' reagent / acetone / 0.5 h / 10 °C 5: 68 percent / lithium, liquid ammonia / tetrahydrofuran; methanol / 1 h / -50 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '605283', constants.ctx, '0')">triethylamine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1909753', constants.ctx, '0')">triphenylemethane</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />&nbsp;1) a) -78 deg C, 5 min, b) 30 min, 2) -78 deg C, 1 h;&nbsp;<br /> &nbsp;