1: 97 percent / pyridine / 18 h / -5 - 0 °C 2: 82 percent / LiAlH4 / diethyl ether / 1.5 h 3: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 4: 92 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 97 percent / pyridine / 18 h / -5 - 0 °C 2: 82 percent / LiAlH4 / diethyl ether / 1.5 h 3: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h 4: 76 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme

1: 97 percent / pyridine / 18 h / -5 - 0 °C 2: 82 percent / LiAlH4 / diethyl ether / 1.5 h 3: 1.) DIBAH, ZrCl4, 2.) O2 / 1.) toluene, hexane, 7 h, 2.) toluene, hexane, from 0 to 60 deg C, 5 h View Scheme

1: 97 percent / pyridine / 18 h / -5 - 0 °C 2: 82 percent / LiAlH4 / diethyl ether / 1.5 h View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4123663', constants.ctx, '0')">diisobutylaluminium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '635760', constants.ctx, '0')">toluene</a> <br />T=-20&deg;C;&nbsp;1.5&nbsp;h;&nbsp;<br /> &nbsp;