Water → HCID 68492039, compound

HRID 21252Notes

Reaction equation

HRID 21252 reaction equation
C([C:3]1[CH:20]=[CH:19][C:6]([C:7]([NH:9][C:10]([CH3:18])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH3:11])=[O:8])=[CH:5][C:4]=1[O:21][CH2:22][O:23][CH3:24])=O.[CH:25]([O:30][CH3:31])([O:28][CH3:29])OC.C(=O)([O-])O.[Na+].O>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:24][O:23][CH2:22][O:21][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][C:3]=1[CH:25]([O:28][CH3:29])[O:30][CH3:31])[C:7]([NH:9][C:10]([CH3:18])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 86628293HCID 86628293, compound

Product 1

HCID 68492039HCID 68492039, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 887MethanolSolvent

Procedure

4-Formyl-3-methoxymethoxy-N-(1-methyl-1-phenylethyl)benzamide (3.12 g, 9.53 mmol) was dissolved in methanol (30 mL), and the solution was added with trimethyl orthoformate (2.09 mL, 19.1 mmol) and p-toluenesulfonic acid monohydrate (16.4 mg, 0.0952 mmol), followed by stirring at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution and water, and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 3-methoxymethoxy-4-dimethoxymethyl-N-(1-methyl-1-phenylethyl)benzamide (3.61 g, yield 100%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d7388f43054845a49d70b9d54500919b
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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