Trichloroisocyanuric Acid → 5-Isopropoxypicolinaldehyde

HRID 1690171

反応式

HRID 1690171 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). The resultant mixture was added with 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 stirred at 0° C. for 5 minutes. The reaction solution was concentrated in vacuo, added with 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 using 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. additionadded with 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

出典と根拠

ORDレコード
ord-d27e2569d0024a778adeb343fc81cafa
出典データセット
uspto-grants-2012_04
特許番号
US08153634B2

関連ノート

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