Ethylene Glycol → HCID 11106179, compound

HRID 534820Notes

Reaction equation

HRID 534820 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][CH:2]1[C:3]([OH:5])=[O:4].I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO.Cl>CC(O)C.O.[Cu]I>[C:10]1([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

9

Reactant 5

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 614proline dl-formHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 11106179HCID 11106179, compoundYield 32.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of D,L-proline (5.00 g, 43.4 mmol), iodobenzene (7.39 g, 36.2 mmol), copper(I) iodide (0.41 g, 2.17 mmol), K3PO4 (15.4 g, 72.4 mmol), and ethylene glycol (4.49 g, 72.4 mmol) in 2-propanol (36 mL) was stirred at 85° C. for 24 h under argon atmosphere. The reaction mixture was cooled to room temperature and diluted with water. The mixture was acidified with 6 M hydrochloric acid solution (pH 3), and extracted with diethyl ether (300 mL), and the extract was washed with water, and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a light brown solid. This solid was triturated with ethyl acetate and washed with diisopropyl ether successively to give the title compound (2.23 g, 27%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with diethyl ether (300 mL)
  3. washthe extract was washed with water, and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford a light brown solid
  8. customThis solid was triturated with ethyl acetate
  9. washwashed with diisopropyl ether successively

Sources & evidence

ORD record
ord-7170104b7c4c4c30809d13a7b15ef7ba
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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