反应详情

温度

-78 °C

LDA (1.3 mL, 2.6 mmol) was added to a solution of methyl propionate (0.22 g, 2.6 mmol) in THF (5 mL) cooled to −78° C. under nitrogen atmosphere. The reaction was stirred for 30 min, and then 4-benzyloxy-benzaldehyde (0.50 g, 2.4 mmol) in THF (5 mL) was added. The reaction was stirred at −78° C. for 5 min, and then allowed to warm to room temperature and stirred overnight. The reaction was partitioned between ethyl acetate and 1N HCl. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting ethyl acetate:hexane (15:85 to 25:75) gradient to give 3-(4-benzyloxy-phenyl)-3-hydroxy-2-methyl-propionic acid methyl ester (0.12 g, 16%) as an oil. MS found: (M+H)+=301.

1. stirringThe reaction was stirred at −78° C. for 5 min
2. temperatureto warm to room temperature
3. stirringstirred overnight
4. customThe reaction was partitioned between ethyl acetate and 1N HCl
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. customto give an oil
9. customThe product was purified by FCC on silica gel
10. washeluting ethyl acetate:hexane (15:85 to 25:75) gradient