1,8-Diazabicyclo(5.4.0)undec-7-ene → Bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate

HRID 966426Notes

Reaction equation

HRID 966426 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][P:5]([O-:12])[O:6][CH2:7][C:8]([F:11])([F:10])[F:9].C1CCN2C(=NCCC2)CC1.[C:26]1([C:32]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:33]2[CH:37]=[C:36]([CH2:38]Cl)[N:35]=[CH:34]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[F:14][C:2]([F:1])([F:13])[CH2:3][O:4][P:5]([CH2:38][C:36]1[N:35]=[CH:34][N:33]([C:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:37]=1)(=[O:12])[O:6][CH2:7][C:8]([F:11])([F:9])[F:10]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 22315069Bis(2,2,2 trifluoroethyl)phosphite

Product 1

HCID 12146930Bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonateYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bis(2,2,2-trifluoroethyl)phosphite (0.11 ml, 0.6 mmol) in THF (1.5 ml) were added 1,8-diazabicyclo[5,4,0]-7-undecene (DBU) (0.09 ml, 0.6 mmol) and (1-triphenylmethylimidazol-4-yl)methyl chloride (71.8 mg, 0.2 mmol). The reaction mixture was refluxed under argon flow for 22 hours. The solvent was removed under reduced pressure, and water (10 ml) was added to the residue, which was then extracted 3 times with ethyl acetate (10 ml). The resultant organic layers were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The obtained white solid was purified through chromatography on silica gel column using ethyl acetate-hexane (3:2) to give bis(2,2,2-trifluoroethyl)(1-triphenylmethylimidazol-4-yl)methylphosphonate (34 mg, 30%) as a white powder. This powder was recrystallized from a mixture of ethyl acetate and hexane to provide a white small needle crystal (m.p. 145-148° C.).

Workup

  1. temperatureThe reaction mixture was refluxed under argon flow for 22 hours
  2. customThe solvent was removed under reduced pressure, and water (10 ml)
  3. additionwas added to the residue, which
  4. extractionwas then extracted 3 times with ethyl acetate (10 ml)
  5. washThe resultant organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe obtained white solid was purified through chromatography on silica gel column

Sources & evidence

ORD record
ord-1fe4d43c966245fda669b0ebad9e7ddb
Source dataset
uspto-grants-2005_10
Patent number
US06951944B2

Reaction notes

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