Methyl iodide → Diethyl 1-(1-triphenylmethylimidazol-4-yl)-ethylphosphonate

HRID 966427Notes

Reaction equation

HRID 966427 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[N:11]=[CH:12][N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[CH3:34]CCCCC.C([Li])CCC.CI>C1COCC1>[C:16]1([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:13]2[CH:14]=[C:10]([CH:9]([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[CH3:34])[N:11]=[CH:12]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 2763175diethyl ((1-(triphenylmethyl)-1H-imidazol-4-yl)methyl)phosphonateHCID 178418339Butyllithium

Product 1

HCID 22315063Diethyl 1-(1-triphenylmethylimidazol-4-yl)-ethylphosphonateYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl(1-triphenylmethylimidazol-4-yl)methylphosphonate (690 mg, 1.5 mmol) in THF (20 ml) was added 1.6M hexane solution of n-butyllithium (0.94 ml, 1.5 mmol) dropwise over 10 minutes at −72° C. under argon flow, followed by adding a solution of methyl iodide (213 mg, 1.5 mmol) in THF (5 ml) dropwise over 10 minutes. After stirring at the same temperature for 30 minutes, the reaction mixture was heated to room temperature, and then stirred at room temperature for 2 hours. The reaction was quenched with water (1 ml), and then the THF was removed under reduced pressure. Saturated brine (40 ml) was added to the residue, and the mixture was extracted 3 times with ethyl acetate (40 ml). The resultant organic layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the crude product as a light yellow solid. It was purified through chromatography on silica gel column using methanol-ethyl acetate (1:9) to provide the titled compound (690 mg, 97%) as a white powder (m.p. 124-126° C.). This powder was recrystallized from a mixture of ethyl acetate and hexane to provide the title compound as a small needle crystal (m.p. 125-128° C.).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. customThe reaction was quenched with water (1 ml)
  3. customthe THF was removed under reduced pressure
  4. additionSaturated brine (40 ml) was added to the residue
  5. extractionthe mixture was extracted 3 times with ethyl acetate (40 ml)
  6. dry with materialThe resultant organic layers were dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product as a light yellow solid
  9. customIt was purified through chromatography on silica gel column

Sources & evidence

ORD record
ord-54f24054529c48aa8ecadff1d66b87a4
Source dataset
uspto-grants-2005_10
Patent number
US06951944B2

Reaction notes

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