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

HRID 460683

반응식

HRID 460683 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1ee15e6341c5421e887b3ba388ee2864
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196111B2

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