Water → Diethyl methyl-(4-acetamido)benzylmalonate

HRID 248062Notes

Reaction equation

HRID 248062 reaction equation
[H-].[Na+].[CH3:3][CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:15]([NH:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Cl)=[CH:21][CH:20]=1)(=[O:17])[CH3:16].O>O1CCCC1>[CH3:3][C:4]([CH2:23][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:15](=[O:17])[CH3:16])=[CH:26][CH:25]=1)([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 148705Acetamide, N-(4-(chloromethyl)phenyl)-

Product 1

HCID 54008305Diethyl methyl-(4-acetamido)benzylmalonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (10.1 g, 0.21 mol) in tetrahydrofuran (300 mL), place under a nitrogen atmosphere and cool to 0° C. Add, by dropwise addition, diethyl methylmalonate (34.8 g, 0.2 mol). Stir for 30 minutes at 0° C. and add 4-acetamidobenzyl chloride (38.6 g, 0.21 mol). Heat at reflux for 5 hours, cool and pour into water (400 mL). Extract with ethyl acetate (3×600 mL), dry (MgSO4) and evaporate the solvent in vacuo to give diethyl methyl-(4-acetamido)benzylmalonate.

Workup

  1. temperatureHeat
  2. temperatureat reflux for 5 hours
  3. temperaturecool
  4. extractionExtract with ethyl acetate (3×600 mL)
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-b9fb229e404a4af4a10cf640f17b2088
Source dataset
uspto-grants-1993_05
Patent number
US05208240

Reaction notes

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