Triethylamine → Methyl 3-(3-cyanophenyl)-5-(dimethoxymethyl)benzoate

HRID 1862572Notes

Reaction equation

HRID 1862572 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH:19]=[O:20])[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:21]([O-])([O-])[O:22]C.O.[C:27]1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>CO>[C:1]([C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([CH:19]([O:22][CH3:21])[O:20][CH3:27])[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521998p-Toluenesulfonic acid monohydrateHCID 9795280Methyl 3-(3-cyanophenyl)-5-(formyl)benzoateHCID 53629101Methylorthoformate

Product 1

HCID 9839713Methyl 3-(3-cyanophenyl)-5-(dimethoxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 200 ml of methanol, were dissolved 2.00 g of the compound obtained in Example 11, 0.86 ml of methyl orthoformate and 0.004 g of p-toluenesulfonic acid monohydrate. The resulting solution was refluxed for 12 hours. After completing the reaction, 0.03 ml of triethylamine was added to the reaction solution, and the solvent was then removed under reduced pressure. Ethyl acetate was added to the residue, and the resulting solution was extracted with ethyl acetate. The organic layer was dried over sodium sulfate. The solvent was removed under reduced pressure to provide 2.35 g (quantitatively) of the title compound.

Workup

  1. temperatureThe resulting solution was refluxed for 12 hours
  2. additionwas added to the reaction solution
  3. customthe solvent was then removed under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. extractionthe resulting solution was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8891fa78ae5b408290049a3f33f94012
Source dataset
uspto-grants-2003_03
Patent number
US06538137B1

Reaction notes

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