toluene-4-sulfonic acid in benzene Heating;

n-butyllithium in tetrahydrofuran T=-78°C; 0.0333333 h;

ZrO(OTf)2 T=20°C; 0.0833333 h; neat (no solvent); chemoselective reaction;

propionaldehyde in tetrahydrofuran under argon; tin-compound in THF cooled to -78 °C; LiBu was added over 10 s; colorless solution after additional 10 s; after 2 min quenched with aldehyde;; poured into NH4Cl-soln. and petroleum ether, shaked 1 min, organic layer sepd., washed (brine), dried (Na2SO4), filtered, concd. (vacuo); chromd. (silica gel; ethyl acetate/petroleum ether 0.5:99.5); (1)H- and (13)C-NMR;;

methanol in tetrahydrofuran under argon; tin-compound in THF cooled to -78 °C; LiBu was added over 10 s; colorless solution after additional 10 s; after 2 min solution was quenched with MeOH;; poured into NH4Cl-soln. and petroleum ether, shaked 1 min, organic layer separated, washed (brine), dried (Na2SO4), filtered, concentrated (vacuo); chromatography (silica gel; ethyl acetate/petroleum ether 0.5:99.5); (1)H- and (13)C-NMR;;

Na-Y-zeolite in dichloromethane 4 h; Heating;

KU-2 resin T=35°C; 5 h;

boron trifluoride diethyl etherate in dichloromethane T=0°C; 3 h; Inert atmosphere; regioselective reaction;

toluene

1: PhBF3(-)K(+) With boron trifluoride diethyl etherate in dichloromethane T=0°C; 0.5 h; Inert atmosphere; 2: O-(methoxymethyl)cyclohexanol in dichloromethane T=23°C; Inert atmosphere; regioselective reaction;