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

HRID 460683

反応式

HRID 460683 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-1ee15e6341c5421e887b3ba388ee2864
出典データセット
uspto-grants-2007_03
特許番号
US07196111B2

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