Trichloroisocyanuric Acid → 5-Isopropoxypicolinaldehyde

HRID 1690171

반응식

HRID 1690171 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 797940465-Isopropoxypicolinaldehyde수율 85%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
0 °C

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-d27e2569d0024a778adeb343fc81cafa
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153634B2

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