Water → HCID 53936350, compound

In dimethylformamide (75 ml) was dissolved methyl (2S,3R)-3-(4-fluorophenyl)-3-hydroxy-2-p-toluenesulfonyloxypropionate (5.48 g, 14.9 mmol), and water (1.4 ml, 74.5 mmol) was added to the solution. The reaction mixture was cooled by an ice bath, potassium carbonate (6.16 g, 44.6 mmol) was added thereto, and the mixture was stirred at room temperature for 22 hours. The reaction mixture was cooled again by an ice bath, water (100 ml) was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. After the solvent was removed, the residue obtained was purified by silica gel column chromatography (diethyl ether/hexane=1/3) to obtain methyl (2R,3R)-3-(4-fluorophenyl)-2,3-epoxypropionate (2.69 g, yield: 92%).

1. additionwas added to the solution
2. temperatureThe reaction mixture was cooled by an ice bath
3. temperatureThe reaction mixture was cooled again by an ice bath
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. customAfter the solvent was removed
8. customthe residue obtained
9. customwas purified by silica gel column chromatography (diethyl ether/hexane=1/3)

ORD record

ord-23d0f90ed0444466bfff0a1c29d31c12

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05677470