Ethylene Glycol → HCID 19047161, compound

HRID 1780647Notes

Reaction equation

HRID 1780647 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([N:10]2[C:15](=[O:16])[CH2:14][CH:13]([C:17]([F:20])([F:19])[F:18])[CH2:12][C:11]2=[O:21])=[C:4]([F:22])[CH:3]=1.[CH2:23]([OH:26])[CH2:24]O.O.[C:28]1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([CH:8]2[O:26][CH2:23][CH2:24][CH2:28][O:9]2)=[CH:6][C:5]([N:10]2[C:11](=[O:21])[CH2:12][CH:13]([C:17]([F:19])([F:18])[F:20])[CH2:14][C:15]2=[O:16])=[C:4]([F:22])[CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 19047150HCID 19047150, compound2×

Product 1

HCID 19047161HCID 19047161, compoundYield 126.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 3.4 g (10 mmol) N-(4'-chloro-2'-fluoro-5'-formylphenyl)-3-(trifluoromethyl)glutarimide (Compound 94) in 110 ml toluene was added 0.94 g (15 mmol) ethylene glycol and a catalytic amount of p-toluenesulfonic acid monohydrate (0.48 g, 2 mmol). The mixture was refluxed for 72 h with removal of water via a Dean-Stark trap. The solvent was removed in vacuo and the residue was partitioned between EtOAc and water. The organics were washed with water and brine, dried over MgSO4, then filtered and concentrated to leave 4.1 g (105% yield) of an oily taffy containing mostly product by NMR analysis. Recrystallization from Et2O afforded 1.0 g of the 1,3-dioxane as a pale yellow solid, m.p. 158°-161° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EtOAc and water
  3. washThe organics were washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto leave 4.1 g (105% yield) of an oily taffy
  8. additioncontaining mostly product by NMR analysis
  9. customRecrystallization from Et2O

Sources & evidence

ORD record
ord-71b357e28ba8447ea602362989a9716c
Source dataset
uspto-grants-1997_05
Patent number
US05631209

Reaction notes

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