Trichloroisocyanuric Acid → 5-Isopropoxypicolinaldehyde

HRID 1038541

反応式

HRID 1038541 の反応式
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][OH:12])=[N:9][CH:10]=1)[CH3:3].CC1(C)N([O])C(C)(C)CCC1.ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O>CC(C)=O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[O:12])=[N:9][CH:10]=1)[CH3:1]

参加物

5

反応物 3

HCID 6909Trichloroisocyanuric AcidHCID 2724126TempoHCID 66598374[5-(Propan-2-yloxy)pyridin-2-yl]methanol

生成物 1

HCID 797940465-Isopropoxypicolinaldehyde収率 85%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

[5-(1-Methylethoxy)pyridin-2-yl]methanol (30 mg, 0.198 mmol) was dissolved in acetone (2.0 mL), added 2,2,6,6-tetramethylpiperidine 1-oxyl (3.1 mg, 0.020 mmol) and trichloroisocyanuric acid (50 mg, 0.218 mmol) under ice-cold conditions, and the mixture was stirred at 0° C. for 5 minutes. The reaction solution was concentrated in vacuo, and the reaction solution was added an aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 5-(1-methylethoxy)-picolinaldehyde (25 mg (yield 85%)) was obtained as a yellow oil.

後処理

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionthe reaction solution was added an aqueous solution of sodium hydrogen carbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-0363204f580243599b7a98c0e406af05
出典データセット
uspto-grants-2013_10
特許番号
US08551985B2

関連ノート

読み込み中…