Ethylene Glycol → HCID 57448072, compound

HRID 1879045Notes

Reaction equation

HRID 1879045 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:14](=[O:16])[CH3:15].[CH2:17](O)[CH2:18][OH:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[C:3]([C:14]2([CH3:15])[O:19][CH2:18][CH2:17][O:16]2)=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 57448071HCID 57448071, compound

Product 1

HCID 57448072HCID 57448072, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(2-fluoro-3-pyridin-4-ylphenyl)ethanone (1.28 g, 5.95 mmol), ethylene glycol (1.66 ml, 29.75 mmol), molecular sieves (5 g, 3 Å) and p-toluenesulfonic acid monohydrate (0.11 g, 0.59 mmol) in toluene (20 ml) was heated at reflux for 2 h. The molecular sieves was filtered off and the residue was evaporated to dryness. Purification by flash column chromatography (ethyl acetate) gave the title compound (1.0 g). MS m/z (rel. intensity, 70 eV) 259 (M+, 1), 245 (15), 244 (bp), 200 (56), 87 (17).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe molecular sieves was filtered off
  4. customthe residue was evaporated to dryness
  5. customPurification by flash column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-8e51e5aed10e4321915b61f2223449ba
Source dataset
uspto-grants-2012_11
Patent number
US08314126B2

Reaction notes

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