Tetrahydrofuran → 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamide

HRID 1857812Notes

Reaction equation

HRID 1857812 reaction equation
[CH3:1][NH2:2].CO.[CH2:5]([O:7][CH:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:24])[C:19](OCC)=[O:20])[CH3:9])[CH3:6].C1COCC1>O>[CH2:5]([O:7][CH:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:24])[C:19]([NH:2][CH3:1])=[O:20])[CH3:9])[CH3:6]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 15390470Ethyl 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-oxoacetateHCID 57454252Monomethylamine methanol

Product 1

HCID 154837862-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamideYield 72.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 40% methylamine-methanol solution (1.63 g, 0.021 mol) was added to a mixed solution of ethyl 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-2-oxoacetate (1.96 g, 0.007 mol) and THF (7 ml) under ice-cooling. The mixture was stirred at room temperature for 1 hour. After completion of the reaction, water (100 ml) was added, and the mixture was extracted with dichloromethane (80 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-N-methyl-2-oxoacetamide (1.35 g, Yield: 72.7%) as a colorless oil.

Workup

  1. temperaturecooling
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (80 ml) twice
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e05687436c2448d5aa5496d87d0ad842
Source dataset
uspto-grants-2000_11
Patent number
US06147231

Reaction notes

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