反应详情

温度

0 °C

To a suspension of 60% by weight sodium hydride oil dispersion (6.97 mmol, 277 mg) in anhydrous tetrahydrofuran (20 mL) cooled to 0° C. was added 2-diphenylphosphinoyl-2-ethoxyacetic acid ethyl ester (3.80 mmol, 1.26 g) followed by [2-(4-formyl-phenyl)-ethyl]-heptyl-carbamic acid tert-butyl ester (3.46 mmol, 1.2 g) dissolved in anhydrous tetrahydrofuran (15 mL). The resulting heterogeneous solution was heated to reflux for one hour. The mixture was cooled to room temperature, quenched by the addition of ethanol (2 mL) and diluted with water (20 mL). The aqueous layer was isolated and extracted with diethyl ether (3×). The organic layers were combined, washed with saturated NaHCO3 (2×), brine (1×), dried over anhydrous sodium sulfate, and concentrated to a crude yellow oil. The crude oil was chromatographed on silica gel (20% ethyl acetate/hexanes) to give 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-ethoxy-acrylic acid ethyl ester as a clear oil (700 mg, 44%).

1. temperatureThe resulting heterogeneous solution was heated
2. temperatureto reflux for one hour
3. temperatureThe mixture was cooled to room temperature
4. customquenched by the addition of ethanol (2 mL)
5. additiondiluted with water (20 mL)
6. customThe aqueous layer was isolated
7. extractionextracted with diethyl ether (3×)
8. washwashed with saturated NaHCO3 (2×), brine (1×)
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated to a crude yellow oil
11. customThe crude oil was chromatographed on silica gel (20% ethyl acetate/hexanes)