HCID 10358783, compound → diethyl (Z)-4-hydroxybut-1-enylphosphonate

Participants

Reaction Steps

A solution of diethyl (Z)-4-(t-butyldimethylsilyloxy)but-1-enylphosphonate (1.32 g, 4.09 mmol) in acetic acid-water (2:1) (35 ml) was stirred at room temperature for 2 hr. The solvent was removed and the residue was purified by column chromatography on silica gel eluting with dichloromethane-methanol (19:1) to give diethyl (Z)-4-hydroxybut-1-enylphosphonate as a colourless liquid (0.5 g, 59%); νmax (film) 3380, 2980, 1720, 1620, 1390, 1230 and 1020 cm-1 ; δH (CDCl3) 1.33 (6H, t, J 7 Hz, CH3), 2.70 (2H, m, CH2), 3.15 (1H, s, OH), 3.73 (2H, t, J 7 Hz, CH2O ), 4.00 (4H, qu, J 7 Hz, CH3CH2), 5.70 (1H, dd, J 14 Hz and 20 Hz, PCH=CH), 6.60 (1H, ddt, J 7 Hz, 14 Hz and 54 Hz, PCH=CH) (Found: MH+ 209.0942. C8H17O4P requires MH+ 209.0943).

Provenance & Evidence