反应详情

温度

80 °C

A stirred suspension of sodium hydride (3.04 g; 60% in mineral oil) in dimethyl sulfoxide (100 ml) was heated at 80° C. for 40 minutes. Then the solution was cooled. To the solution was added (3-carboxypropyl)triphenylphosphonium chloride (15.9 g) portionwise at ambient temperature. After 30 minutes, 2-pyridinecarbaldehyde (3.96 g) was added at ambient temperature and then the mixture was stirred for 2 hours. Water was added to the mixture and acidified to pH 5 with 1N hydrochloric acid. The mixture was extracted with ethyl acetate and combined organic layer was washed with brine, dried, and concentrated. The residue was chromatographed on silica gel ethyl acetate:methanol=10:1) to give (4E)-5-(2-pyridyl)-4-pentenoic acid (1.6 g).

1. temperatureThen the solution was cooled
2. extractionThe mixture was extracted with ethyl acetate and combined organic layer
3. washwas washed with brine
4. customdried
5. concentrationconcentrated
6. customThe residue was chromatographed on silica gel ethyl acetate