Water → HCID 54207351, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 20.2 g (36.8 mmol, 1.3 eq) of 1-triphenylphosphononyl bromide dissolved in 100 ml THF was cooled to -78° C. and 11.9 ml (31.1 mmol, 1.1 eq, 2.6M in hexane) of n-BuLi was added dropwise. This was followed by the dropwise addition of 2.70 ml (156 mmol, 5.5 eq) of hexamethylphosphoroustriamide (HMPA). The solution was stirred for 10 minutes. A solution of 3.0 g (28 mmol) of 4-pyridine carboxaldehyde in 41 ml THF was added. The resulting solution was warmed to room temperature and stirred for 1.75 hours. Water was added to the reaction and this was extracted with Et2O. The organic layer was washed with saturated NH4Cl, followed by saturated NaCl and dried (Na2SO4). The solution was filtered and concentrated in vacuo. Hexanes were added to the residue, decanted and concentrated. The crude material was purified by flash chromatography (15×3 cm, silica gel, 1:5 EtOAc/hexanes) to yield 4.78 g (78%) of title compound as a yellow oil.

Provenance & Evidence