pyridinium chlorochromate in dichloromethane

1: pyridine / 0 °C 2: methanol / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating 4: TsOH / Ambient temperature 5: SO2Cl2 / CH2Cl2 / -40 °C 6: Et3N / CH2Cl2 / -40 - 20 °C 7: Raney Ni W4 / ethanol / Heating 8: LiAlH4 / diethyl ether / Ambient temperature View Scheme

1: pyridine / 0 °C 2: methanol / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating 4: TsOH / Ambient temperature 5: SO2Cl2 / CH2Cl2 / -40 °C 6: Et3N / CH2Cl2 / -40 - 20 °C 7: Raney Ni W4 / ethanol / Heating 8: LiAlH4 / diethyl ether / Ambient temperature 9: TsOH / benzene / Heating View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '10775048', constants.ctx, '0')">titanium(IV) isopropylate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1098280', constants.ctx, '0')">tert.-butylhydroperoxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1727143', constants.ctx, '0')">diethyl (2S,3S)-tartrate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1696917', constants.ctx, '0')">[3.3.1]nonane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-20&deg;C;&nbsp;Sharpless epoxidation;&nbsp;3&nbsp;h;&nbsp;&nbsp;Molecular sieveInert atmosphere;&nbsp;<br /> &nbsp;