Water → Ethyl morpholinoethyl 3-trifluoromethylbenzylphosphonate

HRID 1733822Notes

Reaction equation

HRID 1733822 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)(Cl)=[O:5])[CH3:2].[OH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N(CC)CC)C.O>C(Cl)Cl>[F:17][C:14]([F:15])([F:16])[C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][P:4](=[O:5])([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[O:3][CH2:1][CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 611632-MorpholinoethanolHCID 158191953-Trifluoromethylbenzylphosphonochloridic acid ethyl ester

Product 1

HCID 15818099Ethyl morpholinoethyl 3-trifluoromethylbenzylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Trifluoromethylbenzylphosphonochloridic acid ethyl ester (7.0 mmol)in 20 mL of CH2Cl2 is added slowly to a mixture of N-(2-hydroxyethyl)morpholine and triethylamine (7 mmol) in 20 mL of CH2Cl2 cooled in an ice bath. The resultant mixture is allowed to reach room temperature and is stirred for 5 hours. Water is added (100 mL) and the aqueous phase is extracted 3 times with CH2Cl2 (3×100 mL). The combined organic extracts are dried with anhydrous MgSO4, and evaporated to give the desired product.

Workup

  1. temperaturecooled in an ice bath
  2. customto reach room temperature
  3. extractionthe aqueous phase is extracted 3 times with CH2Cl2 (3×100 mL)
  4. dry with materialThe combined organic extracts are dried with anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-b9a01b15cf394c678d84216bc5754ffa
Source dataset
uspto-grants-1996_07
Patent number
US05532226

Reaction notes

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