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

HRID 342176Notes

Reaction equation

HRID 342176 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. 1H-NMR (CDCl3) δ ppm: 1.17(3H,t,J=7.3), 1.29(3H,d,J=4.9), 2.96(3H,d,J=5.5), 3.41-3.63(2H,m), 4.70-4.92(3H,m), 7.04(1H,brs), 7.33-7.84(4H,m).

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-c0651272be754e5f903ecbcc7ad8b923
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

Loading…