Phosphorus oxychloride → 2,3,4,5-Tetramethoxybenzaldehyde

HRID 1527671

反応式

HRID 1527671 の反応式
CN([CH:9]=[O:10])C1C=CC=CC=1.O=P(Cl)(Cl)Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19]=1[O:28][CH3:29]>C(Cl)Cl.CCOC(C)=O>[CH3:16][O:17][C:18]1[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]([O:24][CH3:25])=[CH:22][C:23]=1[CH:9]=[O:10]

参加物

6

反応物 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 6077731,2,3,4-Tetramethoxybenzene

生成物 1

HCID 6394122,3,4,5-Tetramethoxybenzaldehyde収率 94%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Following the procedure by Syper et al.,19 N-methylformanilide (1.0 mL, 8.1 mmol) was added to a flame dried 10 mL round bottom flask under argon and a drying tube. POCl3 (1.0 mL, 11 mmol) was added at room temperature and the Argon line was removed. After 5 minutes 18 (1.067 g, 5.38 mmol) was dissolved in CH2Cl2 (2.0 mL) and added at room temperature. The reaction was stirred at room temperature under a drying tube for 48 hrs and monitored by 1H NMR. When complete the reaction was diluted with EtOAc, washed with saturated brine, dried over MgSO4, filtered, and condensed. The resulting product was separated from remaining N-methylformanilide using flash chromatography (1:4 Et2O:hexanes) to provide 19 (1.141 g, 5.04 mmol, 94%) as a colorless oil.

後処理

  1. additionwas added to a flame
  2. customdried 10 mL round bottom flask under argon
  3. customthe Argon line was removed
  4. additionadded at room temperature
  5. washwashed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe resulting product was separated

出典と根拠

ORDレコード
ord-c2c45e8f3a8348619eda0bf1daeb2587
出典データセット
uspto-grants-2015_07
特許番号
US09089605B2

関連ノート

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