Ethylene Glycol → HCID 178491322, compound

HRID 455950Notes

Reaction equation

HRID 455950 reaction equation
CO.C(C1C=C[C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[C:13]([OH:32])[C:12]2=[O:33])=CC=1)=O.[CH2:34]([OH:37])[CH2:35][OH:36].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1(C)C=CC=CC=1>[O:36]1[CH2:35][CH2:34][O:37][CH:8]1[N:11]1[CH:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]([C:22](=[O:31])[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[C:13]([OH:32])[C:12]1=[O:33]

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 178491320HCID 178491320, compound

Product 1

HCID 178491322HCID 178491322, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The 0.1M methanol solution of 1-(4-formylphenyl)-3-hydroxy-4-(4-methoxybenzoyl)-5-phenyl-1,5-dihydropyrrol-2-one (1 mL, 0.1 mmol) was concentrated under reduced pressure. Toluene (1 mL), ethylene glycol (0.033 mL, 0.6 mmol) and p-toluenesulfonic acid monohydrate (3.8 mg, 0.02 mmol) was added to the residue. The mixture was heated under azeotropic dehydration for 3 hr. Water (100 mL) was added to the mixture, which was then extracted with ethyl acetate (100 mL). The organic layer was washed with brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the precipitate was collected by filtration and dried to give 1-(1,3-dioxolan-2-yl)-3-hydroxy-4-(4-methoxybenzoyl)-5-phenyl-1,5-dihydro-pyrrol-2-one (3.8 mg, 8%) as pale yellow crystals.

Workup

  1. temperatureThe mixture was heated under azeotropic dehydration for 3 hr
  2. extractionwas then extracted with ethyl acetate (100 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate
  7. filtrationthe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-f2acedf82ea64d01923b5f162a235cb4
Source dataset
uspto-grants-2013_07
Patent number
US08497263B2

Reaction notes

Loading…