反应详情

Methyl (4-fluorophenyl)acetate (0.5 g) was dissolved in DMF (81 mL). The mixture was cooled in an ice bath and NaH (131 mg, 60% w/w in mineral oil) was added. The mixture was stirred for 1 h at RT and again cooled in an ice bath before the addition of MeI (633 mg). The mixture was warmed to RT and, the reaction was quenched with ½ (sat.) aqueous ammonium chloride. Work up consisted of extraction of the aqueous layer with ether (2×). The combined organic fractions were washed with water and brine, then dried (MgSO4). The solvent was evaporated under reduced pressure and methyl 2-(4-fluorophenyl)propanoate was purified on silica gel (ethyl acetate/hexanes). Methyl 2-(4-fluorophenyl)propanoate (420 mg) was dissolved in 12 mL THF and 6 mL MeOH. 6 mL of KOH (2M) was added and the mixture was stirred for 2 h at RT. Water was added and the organic solvents were removed. The base was quenched with icy hydrochloric acid (1N), DCM was added and the phases separated with a phase separator. The solvent was removed under reduced pressure to provide the title compound.

1. temperatureThe mixture was cooled in an ice bath
2. temperatureThe mixture was warmed to RT
3. customthe reaction was quenched with ½ (sat.) aqueous ammonium chloride
4. extractionWork up consisted of extraction of the aqueous layer with ether (2×)
5. washThe combined organic fractions were washed with water and brine
6. dry with materialdried (MgSO4)
7. customThe solvent was evaporated under reduced pressure and methyl 2-(4-fluorophenyl)propanoate
8. customwas purified on silica gel (ethyl acetate/hexanes)
9. dissolutionMethyl 2-(4-fluorophenyl)propanoate (420 mg) was dissolved in 12 mL THF
10. addition6 mL of KOH (2M) was added
11. stirringthe mixture was stirred for 2 h at RT
12. additionWater was added
13. customthe organic solvents were removed
14. customThe base was quenched with icy hydrochloric acid (1N), DCM
15. additionwas added
16. customthe phases separated with a phase separator
17. customThe solvent was removed under reduced pressure