Ethyl benzoylacetate → (-)-Ethyl (S)-3-hydroxy-3-phenylpropionate

Temperature

100 °C

In 0.5 ml of dried and degassed DMF were dissolved 4.9 mg (15 μmol) of (R,R)-t-Bu-QuinoxP*(1) and 3.4 mg (6.7 μmol) of [RuCl2(η6-C6H6)]2 in a nitrogen atmosphere. The mixture was heated at 100° C. for 10 minutes. After cooling to 50° C., the solvent was removed by evaporation under reduced pressure to give a catalyst as a reddish to purple solid. The resulting catalyst was dissolved in 3 ml of degassed ethanol in a glove box. To the solution was added a solution of 129 mg (0.67 mmol) of ethyl 3-oxo-3-phenylpropionate in 1 ml of dichloromethane, and the mixture was transferred into a stainless steel autoclave. After purging the autoclave with hydrogen four times, hydrogen was introduced into the autoclave to 20 atm. The reaction mixture in the autoclave was stirred at 50° C. for 24 hours. After cooling to room temperature, hydrogen gas was released from the autoclave. The solvent was removed, and the residue was dissolved in diethyl ether. The resulting solution was washed successively with water and a sodium chloride aqueous solution, and the organic layer was dried over anhydrous sodium sulfate. Any volatile matter was removed by evaporation, and the residue was purified by silica gel column chromatography to give the title compound, ethyl (S)-3-hydroxy-3-phenylpropionate.

1. customIn 0.5 ml of dried
2. customdegassed DMF
3. temperatureAfter cooling to 50° C.
4. customthe solvent was removed by evaporation under reduced pressure
5. customto give a catalyst as a reddish to purple solid
6. customAfter purging the autoclave with hydrogen four times, hydrogen
7. additionwas introduced into the autoclave to 20 atm
8. temperatureAfter cooling to room temperature
9. customThe solvent was removed
10. dissolutionthe residue was dissolved in diethyl ether
11. washThe resulting solution was washed successively with water
12. dry with materiala sodium chloride aqueous solution, and the organic layer was dried over anhydrous sodium sulfate
13. customAny volatile matter was removed by evaporation
14. customthe residue was purified by silica gel column chromatography

ORD record

ord-c24fd8cf4fe34e66bc19c9c0f768491b

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649117B2