Water → tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

HRID 626413ノート

反応式

HRID 626413 の反応式
C(OP([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29].O>C1COCC1.C(OCC)(=O)C>[Cl:19][C:20]1[CH:27]=[CH:26][C:23](/[CH:24]=[CH:9]/[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:22][C:21]=1[N+:28]([O-:30])=[O:29]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 855054-Chloro-3-nitrobenzaldehydeHCID 2773685tert-Butyl diethylphosphonoacetate

生成物 1

HCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

At 0° C. and with cooling, 156.32 g (620 mmol) of tert-butyl diethylphosphonoacetate were added dropwise to a suspension of 23.71 g (593 mmol) of sodium hydride (60% in mineral oil) in 1.0 liters of THF. After the addition had ended, the mixture was stirred at 0° C. for 30 min and a solution of 100.0 g (539 mmol) of 4-chloro-3-nitrobenzaldehyde in 200 ml of THF was then added. The reaction mixture was heated at RT overnight, and water and ethyl acetate were then added. The organic phase was removed, dried with magnesium sulphate and concentrated under reduced pressure. The residue was recrystallized from isopropanol. Drying under high vacuum gave 144.0 g (94.2% of theory) of the target product.

後処理

  1. additionAfter the addition
  2. temperatureThe reaction mixture was heated at RT overnight
  3. customThe organic phase was removed
  4. dry with materialdried with magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from isopropanol
  7. customDrying under high vacuum
  8. customgave 144.0 g (94.2% of theory) of the target product

出典と根拠

ORDレコード
ord-ea216490ed04416c817834769560509a
出典データセット
uspto-grants-2016_04
特許番号
US09309198B2

反応ノート

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