Triethylamine → HCID 178476786, compound

HRID 483994Notes

Reaction equation

HRID 483994 reaction equation
[CH2:1]([PH:8](=[O:10])[OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:11](N(CC)CC)[CH3:12].C(OC(Cl)=O)C>ClCCl>[CH2:11]([O:10][PH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:9])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 178527042HCID 178527042, compound

Product 1

HCID 178476786HCID 178476786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

13.34 g of benzylphosphinic acid are dissolved in 150 ml of dichloromethane, the solution is cooled to 5°, and 8.64 g of triethylamine are added dropwise. An exothermic reaction takes place. The mixture is cooled to 5° again, and 9.3 g of chloroformic acid ethyl ester are added dropwise within a period of 30 minutes. A precipitate forms in an exothermic reaction with the evolution of gas. The mixture is allowed to warm to room temperature and is then stirred at room temperature for 3 hours, taken up in dichloromethane and washed with water, and the organic solvent is removed. The crude product is distilled under a high vacuum, yielding benzylphosphinic acid ethyl ester having a boiling point of 96°-100° (5×10-6 bar).

Workup

  1. temperaturethe solution is cooled to 5°
  2. customAn exothermic reaction
  3. temperatureThe mixture is cooled to 5° again
  4. customA precipitate forms in an exothermic reaction with the evolution of gas
  5. washwashed with water
  6. customthe organic solvent is removed
  7. distillationThe crude product is distilled under a high vacuum

Sources & evidence

ORD record
ord-081b650ff2164e378f0538a2999c5e12
Source dataset
uspto-grants-1993_07
Patent number
US05229379

Reaction notes

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