Hydrochloric Acid → HCID 10587470, compound

HRID 2289194Notes

Reaction equation

HRID 2289194 reaction equation
[P:1]([O-:6])([O:4][CH3:5])[O:2][CH3:3].[N+:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1)([O-:9])=[O:8].Cl>O1CCCC1>[OH:15][C@@H:14]([P:1](=[O:6])([O:4][CH3:5])[O:2][CH3:3])[C:13]1[CH:12]=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 21884954Dimethylphosphite

Product 1

HCID 10587470HCID 10587470, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl phosphite (37 μl, 0.40 mmol) was added to the solution of ALB in tetrahydrofuran (0.1 M, 0.40 ml) obtained in Example 1 at room temperature. After stirring at room temperature for 30 minutes, the reaction vessel was cooled to -78° C., and it was maintained at this temperature for 15 minutes. Then p-nitrobenzaldehyde (0.40 mmol) was added thereto. After the temperature was raised to room temperature, the stirring was continued for 12 hours. Hydrochloric acid (1N) was added thereto to stop the reaction, and the mixture was extracted with ethyl acetate (10 ml×three times). 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-nitrophenyl)methylphosphonate as a final product in a yield of 81%. The chemical reaction in this Example is shown in chemical formula 31. ##STR25##

Workup

  1. temperaturethe reaction vessel was cooled to -78° C.
  2. temperatureit was maintained at this temperature for 15 minutes
  3. temperatureAfter the temperature was raised to room temperature
  4. waitthe stirring was continued for 12 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)

Sources & evidence

ORD record
ord-47d17fae715c40ef8150c11a6b9dba2e
Source dataset
uspto-grants-2000_07
Patent number
US06090969

Reaction notes

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