反应详情

To an ice cold solution of 500 mg (1.3 mmol) benzoic acid 2,5-dichloro-4-(1-ethoxycarbonyl-1-methyl-ethoxy)-phenyl ester in 11.5 ml methanol was added a solution of 145 mg (6.3 mmol) sodium in 11.5 ml methanol within 5 min under an argon atmosphere. The solution was stirred for 4 h at ambient temperature, cooled to 0° C. and carefully neutralized with 1 N HCl. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and brine/ice water 1/1. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 219 mg (0.8 mmol, 62%) of the title compound as colorless oil.

1. temperaturecooled to 0° C.
2. customThe solvent was removed under reduced pressure
3. dissolutionthe residue was dissolved in ethyl acetate
4. customThe layers were separated
5. extractionthe aqueous layer was extracted two times with ethyl acetate
6. washThe combined organic layers were washed with brine/ice water 1/1
7. dry with materialdried over sodium sulfate
8. customThe solvent was removed under reduced pressure
9. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)