反应详情

温度

-10 °C

Specifically, a solution of 2-(4-benzyloxy-3-methoxyphenyl) acetic acid 15.0 g, 55.1 mmoles) in dry THF (350 mL) was cooled to -78° C. under argon and treated dropwise with n-butyllithium (42 mL, 2.6M in hexanes). The yellow suspension was then allowed to warm to -10° C. and stirred for 60 minutes. A solution of methyl iodide (3.9 mL, 62.6 mmoles) in THF (15 mL total solution) was then added dropwise via syringe over 30 min resulting in a now homogeneous and clear solution. After 2 hours the THF was rotary evaporated and the residue was dissolved in ethyl acetate (500 mL), extracted with 10% phosphoric acid (3×100 mL), extracted with brine (1×100 mL) and dried over magnesium sulfate. Rotary evaporation afforded a yellow oil which solidified on standing. The solid was triturated with n-pentane and filtered to give 2-(4-benzyloxy-3-methoxyphenyl)propionic acid (14.0 g, 89%) as a yellow powder.

1. customresulting in a now homogeneous and clear solution
2. customAfter 2 hours the THF was rotary evaporated
3. dissolutionthe residue was dissolved in ethyl acetate (500 mL)
4. extractionextracted with 10% phosphoric acid (3×100 mL)
5. extractionextracted with brine (1×100 mL)
6. dry with materialdried over magnesium sulfate
7. customRotary evaporation
8. customafforded a yellow oil which
9. customThe solid was triturated with n-pentane
10. filtrationfiltered