lithium aluminium tetrahydride in diethyl ether T=20 - 50°C; 3 h; Heating / reflux;

1: AlCl3 / CH2Cl2 2: LiAlH4; AlCl3 View Scheme

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran / 2 h / -78 °C / |Inert atmosphere 1.2: -78 °C / |Inert atmosphere 2.1: thionyl chloride / methanol / 3 h / |Inert atmosphere; |Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 10 °C / |Inert atmosphere 4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 8 h / |Inert atmosphere; |Reflux 5.1: methyl grignard / tetrahydrofuran / 4 h / 0 - 20 °C / |Inert atmosphere 6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetonitrile / 8 h / 20 °C / |Inert atmosphere 7.1: palladium on activated charcoal; hydrogen / methanol; acetic acid / 10 h / 20 °C / |Inert atmosphere 8.1: sodium periodate / water; acetone / 1 h / |Inert atmosphere 9.1: sodium tetrahydroborate / methanol; water / 1 h / |Inert atmosphere View Scheme

1: methyl grignard / tetrahydrofuran / 4 h / 0 - 20 °C / |Inert atmosphere 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetonitrile / 8 h / 20 °C / |Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol; acetic acid / 10 h / 20 °C / |Inert atmosphere 4: sodium periodate / water; acetone / 1 h / |Inert atmosphere 5: sodium tetrahydroborate / methanol; water / 1 h / |Inert atmosphere View Scheme

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

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

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