Hydrochloric Acid → dimethyl (S)-hydroxy(p-methylphenyl)methylphosphonate

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 at room temperature for 30 minutes, the reaction vessel was cooled to -40° C., and it was maintained at this temperature for 15 minutes. Then p-methylbenzaldehyde (0.40 mmol) was added thereto. After reacting for 92 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)-hydroxy(p-methylphenyl)methylphosphonate as a final product in a yield of 82%. The chemical reaction in this Example is shown in chemical formula 29.

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. temperaturethe reaction vessel was cooled to -40° C.
4. temperatureit was maintained at this temperature for 15 minutes
5. waitAfter reacting for 92 hours
6. customthe reaction
7. extractionThe mixture was extracted with ethyl acetate (10 ml×three times)
8. washthe combined extracts were washed with brine
9. dry with materialdried over Na2SO4
10. distillationThe solvent was distilled
11. customthe residue was purified by flash column chromatography (acetone/hexane=1/5, on SiO2)

ORD record

ord-2bdee10a79814009899cd2fe9e77250c

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05847186