thionyl chloride T=0 - 20°C; 16 h; Inert atmosphere;

sodium tetrahydroborate in methanol T=5 - 10°C; 2 h;

zinc in diethyl ether; toluene Alkylation; 1.5 h; Heating;

1: 2-propenylmagnesium bromide / diethyl ether / 1 h / -42 - 20 °C / |Inert atmosphere 2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 32 h / 20 °C / |Inert atmosphere 3: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 4: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 16 h / 20 °C / |Inert atmosphere 5: thionyl chloride / 16 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 16 h / 20 °C / |Inert atmosphere 2: thionyl chloride / 16 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 32 h / 20 °C / |Inert atmosphere 2: sodium periodate / water; tetrahydrofuran / 2 h / 20 °C / |Inert atmosphere 3: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol / 16 h / 20 °C / |Inert atmosphere 4: thionyl chloride / 16 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: 3 h / Heating 2: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

1: pyridine / CH2Cl2 / 0 deg C, 1 h then r.t., 4 h 2: 3 h / Heating 3: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

sodium hydroxide in methanol Ambient temperature; Yield given;