sodium tetrahydroborate in propan-1-ol T=20°C;

sodium borohydride in tetrahydrofuran

in tetrahydrofuran byproducts: phenylboronic acid; to srirred soln. of Sn-compound in THF was added soln. of BH3 in THF under N2, mixt. was left at room temp. for 1 h, refluxed for 1 h, cooled, Et2O and water was added; dried with MgSO4, solvent was removed under vac., column chromy. on silica gel with hexane and hexane-Et2O, recrystd. from water;

in diethyl ether

1: n-heptane; diethyl ether / 0 - 20 °C / |Inert atmosphere 2: iodine / methanol / 60 °C / |Reflux 3: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 4: sodium tetrahydroborate / propan-1-ol / 20 °C View Scheme

1: iodine / methanol / 60 °C / |Reflux 2: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 3: sodium tetrahydroborate / propan-1-ol / 20 °C View Scheme

1: hydrogenchloride / n-heptane; water / 0.5 h / 20 °C 2: sodium tetrahydroborate / propan-1-ol / 20 °C View Scheme

in diethyl ether