Ethylene Glycol → HCID 329362, 화합물

HRID 473403

반응식

HRID 473403 반응식
[N+:1]([C:4]1[C:5]([CH:10]=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:11]1[CH2:23][CH2:24][O:25][CH:10]1[C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=[CH:7][N:6]=1

참가 물질

7

반응물 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 3293613-Nitropicolinaldehyde

생성물 1

HCID 329362HCID 329362, 화합물

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

3-Nitro-2-pyridinecarbaldehyde (22 g, 144.74 mmol) was dissolved in toluene (500 mL). To the mixture was added catalytic amount of p-TSA (2 g) and ethylene glycol (40 mL) and the reaction flask equipped with Dean-Stark assembly was refluxed for 12 h at 120° C. After the reaction was complete, the reaction mixture was treated with water and ethyl acetate. The organic layer was separated and the aqueous layer was back extracted with ethyl acetate. The organic layers were combined and dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a thick oily mass. The oily mass was then purified by silica gel column chromatography using 20% of ethyl acetate and hexane as eluent to give 2-(1,3-dioxolan-2-yl)-3-nitropyridine: 1H-NMR (CDCl3) δ: 4.2 (d, 5H), 6.5 (s, 1H), 7.5 (m, 1H), 8.3 (d, 1H), 8.9 (brs, 1H).

후처리

  1. customthe reaction flask equipped with Dean-Stark
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was back extracted with ethyl acetate
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto give a thick oily mass
  7. customThe oily mass was then purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0e6942b0b24047c6b74d017462bca360
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633313B2

연결된 노트

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