p-Toluenesulfonic acid → 2-Nitrobenzeneacetaldehyde

HRID 538073

反応式

HRID 538073 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11](=[O:15])C(O)=O)([O-:3])=[O:2].N1CCOCC1.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]=[O:15])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 795833-(2-Nitrophenyl)-2-oxopropanoic acid

生成物 1

HCID 108447642-Nitrobenzeneacetaldehyde収率 325.2%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

To a solution of 2-Nitrophenylpyruvic acid (1.3 g, 6.22 mmol) in dry dioxane 12 mL was added morpholine (1.5 ml, 17.23 mmol) and a catalytical quantity of p-TSA. Then the resulting mixture was firstly sonicated and then heated in microwave conditions at 120° C. for 30 min. Dioxane was evaporated at reduced pressure and the crude vigourously stirred in 1/1 EtOAc/H2O (10 mL) overnight. The organic layer was separated and the aqueous phase washed with EtOAc (×2). The combined organic layer was dried over Na2SO4 anhydrous and solvent was removed at reduced pressure. Finally, the crude product was purified by flash chromatography on silica (ETP to 1:1 ETP/EtOAc) to obtain the titled compound (3.34 g, yield 64%).

後処理

  1. customThen the resulting mixture was firstly sonicated
  2. customDioxane was evaporated at reduced pressure
  3. customThe organic layer was separated
  4. washthe aqueous phase washed with EtOAc (×2)
  5. dry with materialThe combined organic layer was dried over Na2SO4 anhydrous and solvent
  6. customwas removed at reduced pressure
  7. customFinally, the crude product was purified by flash chromatography on silica (ETP to 1:1 ETP/EtOAc)

出典と根拠

ORDレコード
ord-9c7f1f3515c444c5a1104dbcc7613dea
出典データセット
uspto-grants-2014_10
特許番号
US08865704B2

関連ノート

読み込み中…