1: thionyl chloride / methanol / 3 h / |Inert atmosphere; |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 10 °C / |Inert atmosphere 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 8 h / |Inert atmosphere; |Reflux 4: methyl grignard / tetrahydrofuran / 4 h / 0 - 20 °C / |Inert atmosphere 5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetonitrile / 8 h / 20 °C / |Inert atmosphere 6: palladium on activated charcoal; hydrogen / methanol; acetic acid / 10 h / 20 °C / |Inert atmosphere 7: sodium periodate / water; acetone / 1 h / |Inert atmosphere 8: sodium tetrahydroborate / methanol; water / 1 h / |Inert atmosphere View Scheme