Triethylamine → Diethylaminoethyl ethyl 3-trifluoromethylbenzylphosphonate

HRID 1463567Notes

Reaction equation

HRID 1463567 reaction equation
[CH2:1]([O:3][P:4]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:6])[OH:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH2:24]([N:26]([CH:29](O)[CH3:30])[CH2:27][CH3:28])[CH3:25].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[F:16][C:14]([F:15])([F:17])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:25][CH2:24][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15819194Ethyl 3-trifluoromethylbenzylphosphonic acidHCID 158948401-(Diethylamino)ethanol

Product 1

HCID 15819197Diethylaminoethyl ethyl 3-trifluoromethylbenzylphosphonateYield 10.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Ethyl 3-trifluoromethylbenzylphosphonic acid, (7.55 g, 28 mmol) was dissolved in 100 mL of CH2Cl2 and cooled to 0° C. under nitrogen. After the oxalyl chloride (28 mmol) had been added, 0.5 mL of DMF was slowly added in 3 portions, and the resultant mixture was stirred at room temperature for 3 hours. Evaporation in vacuo gave the crude acid chloride which was dissolved in 90 mL of CH2Cl2 and added dropwise to a mixture of N,N-diethylaminoethanol (3.29 g, 28 mmol) and triethylamine (3.42 g, 34 mmol) in 60 mL of CH2Cl2 cooled at 0° C. The resultant mixture was allowed to warm to room temperature and stirred for 4 hours. Water was added (100 mL) and the aqueous phase was extracted 3 times with CH2Cl2. The combined organic extracts were dried with anhydrous Na2SO4, and evaporated to give the crude product as an oil. Purification was accomplished through column chromatography on silica gel using CH2Cl2 containing 2% MeOH and 0.1% NH3 and gave 1.1 g of the analytical product as an orange oil. D.C.I.M.S.[MH+, 368].

Workup

  1. customEvaporation in vacuo
  2. customgave the crude acid chloride which
  3. temperaturecooled at 0° C
  4. temperatureto warm to room temperature
  5. extractionthe aqueous phase was extracted 3 times with CH2Cl2
  6. dry with materialThe combined organic extracts were dried with anhydrous Na2SO4
  7. customevaporated
  8. customto give the crude product as an oil
  9. customPurification

Sources & evidence

ORD record
ord-a5da0c5454e14827b701b62ccd43ae1a
Source dataset
uspto-grants-1994_04
Patent number
US05300687

Reaction notes

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