Triethyl phosphonoacetate → Ethyl 3-(2,3,4-trimethoxyphenyl)prop-2-enoate

HRID 1267625

反応式

HRID 1267625 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[CH:23][C:20]=1[CH:21]=O>C1COCC1>[CH3:17][O:18][C:19]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[CH:23][C:20]=1[CH:21]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 750062,3,4-Trimethoxybenzaldehyde

生成物 1

HCID 67200008Ethyl 3-(2,3,4-trimethoxyphenyl)prop-2-enoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydride (60% dispersion in mineral oil; 245 mg) was suspended in THF (1 mL) under an argon atmosphere, to the suspension ethyl diethylphosphonoacetate (1.11 mL) was added dropwise under ice cooling, and the mixture was stirred for 30 minutes. After 2,3,4-trimethoxybenzaldehyde (1.0 g) was then added to the mixture, the reaction mixture was stirred at room temperature for 30 minutes and concentrated under reduced pressure. The residue was dissolved in chloroform, and the solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

後処理

  1. additionwas added dropwise under ice cooling
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washthe solution was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-ad0405e069a04048add29f64914eab36
出典データセット
uspto-grants-2003_04
特許番号
US06552188B2

関連ノート

読み込み中…