Sodium hydride → Methyl (2E)-3-(1-methyl-1H-imidazol-4-yl)-2-propenoate

HRID 540410ノート

反応式

HRID 540410 の反応式
C(OP([CH2:9][C:10]([O:12][CH3:13])=[O:11])(OCC)=O)C.[H-].[Na+].[CH3:16][N:17]1[CH:21]=[C:20]([CH:22]=O)[N:19]=[CH:18]1>O1CCCC1>[CH3:16][N:17]1[CH:21]=[C:20](/[CH:22]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])[N:19]=[CH:18]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 5734191-Methyl-1H-imidazole-4-carbaldehyde

生成物 1

HCID 13944045Methyl (2E)-3-(1-methyl-1H-imidazol-4-yl)-2-propenoate収率 57.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

1 ml (5.5 mmol) of methyl diethylphosphonoacetate are added to a suspension of 220 mg (5.5 mmol) of sodium hydride at 60% in 5 ml of tetrahydrofuran cooled to 0° C. After stirring for 1 h, 500 mg (4.5 mmol) of 1-methyl-1H-imidazole-4-carbaldehyde are added and the mixture is stirred for 4 hours at ambient temperature and then hydrolysed with water and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over magnesium sulphate, filtered and evaporated. The product obtained is precipitated from heptane and filtered. 430 mg of methyl (E)-3-(1-methyl-1H-imidazol-4-yl)acrylate are obtained in the form of a yellow powder with a yield of 57%.

後処理

  1. stirringthe mixture is stirred for 4 hours at ambient temperature
  2. extractionhydrolysed with water and extracted with ethyl acetate
  3. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe product obtained
  8. customis precipitated from heptane
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-5e3b943bd15746d69f4f64761bc1fcd9
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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