Cesium carbonate → HCID 86672917, compound

HRID 242761Notes

Reaction equation

HRID 242761 reaction equation
[PH:1](=[O:16])([O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[O:2][CH2:3][CH2:4][Si:5]([CH3:8])([CH3:7])[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([O:33][N:34]2[C:39]([CH3:41])([CH3:40])[CH2:38][CH2:37][CH2:36][C:35]2([CH3:43])[CH3:42])[CH3:32])=[CH:27][CH:26]=1>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:13][Si:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][O:9][P:1]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([O:33][N:34]2[C:39]([CH3:41])([CH3:40])[CH2:38][CH2:37][CH2:36][C:35]2([CH3:42])[CH3:43])[CH3:32])=[CH:27][CH:26]=1)(=[O:16])[O:2][CH2:3][CH2:4][Si:5]([CH3:7])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 58903334HCID 58903334, compoundHCID 178504284HCID 178504284, compound

Product 1

HCID 86672917HCID 86672917, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound I, that is, bis[2-(trimethylsilyl)ethyl] phosphonate (582 mg, 2.05 mmol) is dissolved in dimethylformamide (“DMF”) (25 ml) to manufacture a solution III-1. Cesium carbonate (Cs2CO3)) (2 g, 6.13 mmol) and tetrabutylammonium iodide (“TBAI”) (2.26 g, 6.13 mmol) are added to the solution III-1, and stirred at room temperature for approximately 1 hour under a nitrogen atmosphere to manufacture a solution III-2. After approximately 1 hour, compound II, that is, 1-[1-(4-chloromethylphenyl)ethoxy]-2,2,6,6-tetramethyl-piperidine (1.9 g, 6.13 mmol), is added to the solution III-2, and stirred for approximately 24 hours to manufacture a suspension III-3. The suspension III-3 is purified with ethyl acetate (“EtOAc”), washed with distilled water, dried over anhydrous magnesium sulfate (MgSO4), and then condensed under a vacuum to obtain non-purified {4-[1-(2,2,6,6-tetramethyl-piperidine-1-yloxy)-ethyl]-benzyl}-phosphonic acid bis-(2-trimethylsilylethyl) ester.

Workup

  1. waitAfter approximately 1 hour
  2. stirringstirred for approximately 24 hours
  3. customThe suspension III-3 is purified with ethyl acetate (“EtOAc”)
  4. washwashed with distilled water
  5. dry with materialdried over anhydrous magnesium sulfate (MgSO4)
  6. customcondensed under a vacuum

Sources & evidence

ORD record
ord-c1181f94c77f498e9c8d6dd8ae278cd2
Source dataset
uspto-grants-2014_02
Patent number
US08653211B2

Reaction notes

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