反应详情

温度

50 °C

Propyl iodide (41.6 mmol) was added at room temperature to a solution of (2S)-3-(4-benzyloxy-phenyl)-2-hydroxy-propionic acid ethyl ester (Example 377, Step 2) (8.3 mmol) and silver oxide (12.45 mmol) in 40 mL of DMF. The mixture was heated at 50° C. for 24 hours. After that the mixture was cooled to room temperature, 300 ml of ethyl acetate and 200 ml of water were added. The aqueous layer was separated and the organic layer were washed with brine (3×100 ml), and then dried over (MgSO4), filtered and concentrated under vacuum. The crude was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1) to produce a yellow oil. 1H-NMR (CDCl3, 200.15 MHz): 7.42–7.31 (m, 5 H), 7.17 (d, 2 H, J=8.6 Hz), 6.90 (d, 2 H, J=8.6 Hz), 5.05 (s, 2 H), 4.17 (q, 2 H, J=7.0 Hz), 3.97 (dd, 1 H, J=7.0, 6.2 Hz), 3.53 (dt, 1 H, J=8.9, 6.4 Hz), 3.23 (dt, 1 H, J=9.1, 6.7 Hz), 2.97 (d, 2 H, J=6.7 Hz), 1.66–1.48 (m, 2 H), 1.23 (t, 3 H, J=7.3 Hz), 0.86 (t, 3 H, J=7.5 Hz).

1. temperatureAfter that the mixture was cooled to room temperature
2. customThe aqueous layer was separated
3. washthe organic layer were washed with brine (3×100 ml)
4. dry with materialdried over (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe crude was purified by chromatography (silica gel, hexanes/ethyl acetate 6:1)
8. customto produce a yellow oil