反应详情

A suspension of benzyl 2-(4-((2-(benzyloxy)ethoxy)methyl)-3-fluorophenyl)acrylate (2.2 g, 5.23 mmol), 10% Pd(OH)2 (300 mg) in EtOAc (20 mL) was hydrogenated (balloon pressure) at RT for 2 h until complete consumption of benzyl 2-(4-((2-(benzyloxy)ethoxy)methyl)-3-fluorophenyl)acrylate, as evidenced by TLC analysis. The reaction mixture was filtered through Celite, washed with MeOH (2×15 mL). The combined filtrate was concentrated and the obtained crude compound was purified by dissolving in EtOAc (30 mL) and shaken with aq 10% NaHCO3 solution (12 mL). The EtOAc layer was separated; the aq layer was acidified with aq. citric acid solution (pH˜5) and extracted with EtOAc (2×30 mL). The combined EtOAc layer was washed with water (10 mL), brine (10 mL) dried over anhydrous NaSO4, filtered and concentrated to afford 2-(3-fluoro-4-((2-hydroxyethoxy)methyl)phenyl)propanoic acid (450 mg, 36%) as colorless oil (TLC solvent system: 100% EtOAc; Rf: 0.15).

1. customat RT
2. customfor 2 h
3. customuntil complete consumption of benzyl 2-(4-((2-(benzyloxy)ethoxy)methyl)-3-fluorophenyl)acrylate
4. filtrationThe reaction mixture was filtered through Celite
5. washwashed with MeOH (2×15 mL)
6. concentrationThe combined filtrate was concentrated
7. customthe obtained crude compound
8. customwas purified
9. dissolutionby dissolving in EtOAc (30 mL)
10. customThe EtOAc layer was separated
11. extractionextracted with EtOAc (2×30 mL)
12. washThe combined EtOAc layer was washed with water (10 mL), brine (10 mL)
13. dry with materialdried over anhydrous NaSO4
14. filtrationfiltered
15. concentrationconcentrated