Ethylene Glycol → HCID 59556957, compound

HRID 1967308Notes

Reaction equation

HRID 1967308 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](I)[CH:8]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>CC(O)C.[Cu](I)I.O>[Cl:6][C:7]1[CH:8]=[C:9]([NH:1][C@@H:2]([CH3:5])[CH2:3][OH:4])[CH:10]=[CH:11][CH:12]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 122691-Chloro-3-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 80307L-Alaninol

Product 1

HCID 59556957HCID 59556957, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of (2S)-2-aminopropan-1-ol (11.7 g), 1-chloro-3-iodobenzene (36.1 g), tripotassium phosphate (66.4 g), copper iodide (1.42 g), and ethylene glycol (16.7 mL) in propane-2-ol (155 mL) was stirred at 80° C. for 24 hr under an argon atmosphere. Water (500 mL) was added to the reaction solution, and the mixture was extracted with diethyl ether. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%) to give the title compound as a colorless oil (yield: 26.9 g, 97%).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%)

Sources & evidence

ORD record
ord-f69c49211cf046fa8bf781e5e7711225
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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