Ethylene Glycol → 3-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester

HRID 1360779Notes

Reaction equation

HRID 1360779 reaction equation
COC1C=CC(NC2OC(C3C=CC4N=[C:21]([C:23]5[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:25][C:24]=5[CH3:35])NC=4C=3)=NN=2)=CC=1.[CH2:37]([OH:40])[CH2:38][OH:39].[CH3:41]C1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:41][O:34][C:32](=[O:33])[CH2:31][CH2:30][C:26]1[CH:25]=[C:24]([CH3:35])[C:23]([CH:21]2[O:40][CH2:37][CH2:38][O:39]2)=[C:28]([CH3:29])[CH:27]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 252354053-(4-{6-[5-(4-Methoxyphenylamino)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-propionic acid

Product 1

HCID 669660773-(4-[1,3]Dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 3-(4-formyl-3,5-dimethylphenyl)-propionic acid methyl ester (prepared as described in Example 1-60, 2.2 g, 10 mmol) and ethane-1,2-diol (1.86 g, 30 mmol) in toluene (50 mL) was added p-TsOH.H2O (38 mg, 0.2 mmol) and the solution was refluxed using a Dean-Stark apparatus overnight. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) as eluent to give 3-(4-[1,3]dioxolan-2-yl-3,5-dimethylphenyl)-propionic acid methyl ester as a colorless oil.

Workup

  1. temperaturethe solution was refluxed
  2. customa Dean-Stark apparatus overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a41ca3d733b54f07acfde46285adb212
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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