Benzaldehyde → HCID 10910925, compound

Temperature

-40 °C

The solution of ALB in tetrahydrofuran (0.1M, 0.40 ml) obtained in Example 1 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., and it was maintained at this temperature for 15 minutes. Benzaldehyde (0.40 mmol) then was added thereto. After reacting for 51 hours, 1N hydrochloric acid was added thereto to stop the reaction. The mixture was extracted with ethyl acetate (10 ml×three times). The combined extracts were washed with brine and dried over Na2 SO4. The solvent was distilled, and the residue was purified by flash column chromatography (acetone/hexane=1/5, on SiO2) to obtain dimethyl (S)-hydroxy-phenylmethylphosphonate as final product in a yield of 90%. The chemical reaction in this Example is shown in chemical formula 27.

1. concentrationThe solution of ALB in tetrahydrofuran (0.1M, 0.40 ml) obtained in Example 1 was concentrated at room temperature for 1 hour under reduced pressure
2. addition0.4 ml of toluene was added
3. temperatureit was maintained at this temperature for 15 minutes
4. waitAfter reacting for 51 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. customdried over Na2 SO4
9. distillationThe solvent was distilled
10. customthe residue was purified by flash column chromatography (acetone/hexane=1/5, on SiO2)

ORD record

ord-db4668ccf292413c8cad13357769527f

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05847186