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

Temperature

-20 °C

The compound of Example 45 shown in Table 9 (14 mg, 0.05 mmol) was added to titanium tetrachloride (9.5 mg, 0.05 mmol) in toluene (1.0 ml), and the resultant mixture was stirred until the mixture became uniform. After titanium was coordinated with the compound, the solvent was removed through evaporation under reduced pressure at room temperature. The resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml), and the solution was cooled to −20° C. Separately, benzaldehyde (106 mg, 1.0 mmol) and 1-ethoxy-1-trimethylsiloxyethene (192 mg, 1.2 mmol) were dissolved in anhydrous tetrahydrofuran (2 ml), and the resultant solution was added to the above solution, and then the resultant mixture was stirred at −20° C. for one day. Tetrahydrofuran (2 ml) containing trifluoroacetic acid in an amount of 10 w/w% was added to the resultant reaction mixture, and the mixture was returned to room temperature. The reaction mixture was diluted with water, and then subjected to extraction with ether. The organic layer was washed with salt water, and dried over anhydrous magnesium sulfate. After removal of the solvent, the resultant oily product was purified through silica gel chromatography, to thereby yield colorless oily ethyl (S)-3-hydroxy-3-phenylpropionate ([α]D20-25.5 (cl, CHCl3)) at a yield of 70%.

1. customthe solvent was removed through evaporation under reduced pressure at room temperature
2. dissolutionThe resultant residue was dissolved in anhydrous tetrahydrofliran (10 ml)
3. additionw/w% was added to the resultant
4. customreaction mixture
5. customwas returned to room temperature
6. extractionsubjected to extraction with ether
7. washThe organic layer was washed with salt water
8. dry with materialdried over anhydrous magnesium sulfate
9. customAfter removal of the solvent
10. customthe resultant oily product was purified through silica gel chromatography

ORD record

ord-5751bbdbb8b041d09af35c66f0c3f6df

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303796B1