N,N-Dimethylglycine → HCID 67528903, compound

HRID 1867554Notes

Reaction equation

HRID 1867554 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>O1CCOCC1.C(OCC)(=O)C.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 673N,N-DimethylglycineHCID 46844-ChlorophenolHCID 10796Cesium carbonateHCID 30407702-(4-Iodophenyl)ethan-1-ol

Product 1

HCID 67528903HCID 67528903, compoundYield 59.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1.14 g (4.60 mmol) of 2-(4-iodophenyl)ethanol, 0.88 g (6.89 mmol) of 4-chlorophenol, 2.99 g (9.20 mmol) of cesium carbonate, 0.14 g (1.38 mmol) of N,N-dimethylglycine and 0.087 g (0.46 mmol) of cuprous iodide in 4 ml of dioxane is heated at 90° C. for 24 hours with thorough stirring under an argon atmosphere. It is cooled to ambient temperature and taken up in 150 ml of ethyl acetate and 50 ml of water. After the phases have settled and been separated, the organic phase is washed with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution, dried over magnesium sulphate and evaporated to dryness. The residue is purified by chromatography on silica gel, eluting with an 85/15 then 75/25 mixture of cyclohexane and ethyl acetate, to give 0.68 g of product in the form of an oil.

Workup

  1. temperatureIt is cooled to ambient temperature
  2. custombeen separated
  3. washthe organic phase is washed with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness
  6. customThe residue is purified by chromatography on silica gel
  7. washeluting with an 85/15
  8. addition75/25 mixture of cyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-2ecfdd2e86664c438edbfda6b02029a2
Source dataset
uspto-grants-2009_12
Patent number
US07632850B2

Reaction notes

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