Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 86748310, compound

Participants

Reaction Steps

To a solution of 9.75 g (0.0292 mol) of (2S,3S,4S)-4-(t-butyldimethylsilyloxy)2-(3-pyridyl)tetrahydrofuran-3-carboxaldehyde in 120 ml of methylene chloride is added 9.75 g (0.0292 mol) of methyl (triphenylphosphoranylidene)acetate, the mixture is stirred at room temperature overnight and evaporated. The residue is triturated with ether to precipitate out most of the triphenylphosphine oxide, filtered and washed with ether. The filtrates are evaporated and the residue is purified by flash chromatography from silica gel (5×9 cm2) using methylene chloride-ethyl acetate (1:1) as eluent to give 6.77 g of methyl (E)-(2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]-2-propenoate with elemental analysis: C, 62.67; H, 8.12; N, 3.86 (theory: C, 62.78, H, 8.04; N, 3.85) and optical rotation [α]D 25=+26.77 (8.9 mg/ml methanol).

Provenance & Evidence