1-methoxy-N,N,N',N'-tetramethylmethylenediamine → Methyl 2-[4-(benzyloxy)phenyl]-3-dimethylamino-2-propenoate

HRID 460683

Reaction equation

HRID 460683 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.CO[CH:22](N(C)C)[N:23]([CH3:25])[CH3:24]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:19])[C:4]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)=[CH:22][N:23]([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 709081-methoxy-N,N,N',N'-tetramethylmethylenediamineHCID 2756645Methyl 2-(4-benzyloxyphenyl)acetate

Product 1

HCID 69154646Methyl 2-[4-(benzyloxy)phenyl]-3-dimethylamino-2-propenoateYield 99.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

According to a modified literature procedure (Wasserman, H. H.; Ives, J. L. J. Org. Chem. 1985, 50, 3573–3580) a solution of 1.0 g (3.9 mmol) of (4-benzyloxy-phenyl)-acetic acid methyl ester in 4 mL of toluene was flushed with argon. To this solution was added 0.842 mL g (5.5 mmol) of methoxy bis(dimethylamino)methane, and the resulting mixture was stirred at 65° C. under argon overnight. The reaction mixture was concentrated to give 1.21 g of desired 2-(4-benzyloxy-phenyl)-3-dimethylamino-acrylic acid methyl ester as indicated by 1H NMR (containing traces of starting material). The product was used without any further purification in the next step.

Workup

  1. customwas flushed with argon
  2. additionTo this solution was added 0.842 mL
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1ee15e6341c5421e887b3ba388ee2864
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Linked notes

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