Benzaldehyde → HCID 10910925, compound

Temperature

-40 °C

The solution of the Al--Li-(R)-binaphthol complex (hereinafter abbreviated as ALB) obtained in Example 1 in tetrahydrofuran (0.1 M, 0.36 ml) was concentrated at room temperature for 1 hour under reduced pressure, then 0.4 ml of toluene was added thereto under an argon atmosphere. To this solution was added dimethyl phosphite (37 μl, 0.40 mmol) at room temperature. After stirring for 30 minutes, the reaction vessel was cooled to -40° C. After it was maintained at this temperature for 15 minutes, benzaldehyde (0.48 mmol) was added thereto. After reacting for 90 hours, 1N hydrochloric acid was added thereto to stop the reaction. The mixture was extracted with ethyl acetate (10 ml×three times), and the combined extracts were washed with brine and dried over Na2SO4. The solvent was distilled, and the residue was purified by flash column chromatography (acetone/hexane=1/5, on SiO2) to obtain dimethyl (S)-hydroxyphenylmethylphosphonate as a final product in a yield of 95%. The chemical reaction in this Example is shown in chemical formula 26. ##STR20##

1. concentrationwas concentrated at room temperature for 1 hour under reduced pressure
2. addition0.4 ml of toluene was added
3. temperatureAfter it was maintained at this temperature for 15 minutes
4. waitAfter reacting for 90 hours
5. customthe reaction
6. extractionThe mixture was extracted with ethyl acetate (10 ml×three times)
7. washthe combined extracts were washed with brine
8. dry with materialdried over Na2SO4
9. distillationThe solvent was distilled
10. customthe residue was purified by flash column chromatography (acetone/hexane=1/5, on SiO2)

ORD record

ord-72d77e55cabc452d8731d63f5d6f4165

Source dataset

uspto-grants-2000_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06090969