Ethylene Glycol → HCID 117607156, compound

HRID 588790Notes

Reaction equation

HRID 588790 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([O:6][C:7]2[CH:12]=[C:11](Cl)[CH:10]=[CH:9][N:8]=2)=[C:4]([I:17])[CH:3]=1.[CH2:18]([OH:21])[CH2:19][OH:20].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]([O:6][C:7]2[CH:12]=[C:11]([O:20][CH2:19][CH2:18][OH:21])[CH:10]=[CH:9][N:8]=2)=[C:4]([I:17])[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 11430Potassium CarbonateHCID 117607159HCID 117607159, compound

Product 1

HCID 117607156HCID 117607156, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(4,5-dichloro-2-iodophenoxy)-4-chloropyridine (0.45 g, 1.128 mmol), ethane-1,2-diol (4 mL, 71.89 mmol), K2CO3 (0.45 mg, 3.26 mmol) in acetone (6 mL) was stirred at 120° C. for 5 h. The mixture was poured into water and extracted with ethyl acetate. The organic layer was washed withed brine, dried over Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 4:1) to afford the desired product (160 mg, 33% yield). ESI-MS m/z: 426.0[M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 4:1)

Sources & evidence

ORD record
ord-cf6b9beaea7e4258aa17d8bb971782fb
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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