Ethylene Glycol → 2-(1,3-Dioxolan-2-yl)-5-fluoro-3-nitropyridine

HRID 473424노트

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HRID 473424 반응식
[F:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](O)[CH2:25][OH:26].O>C1(C)C=CC=CC=1>[O:9]1[CH2:24][CH2:25][O:26][CH:8]1[C:5]1[C:4]([N+:10]([O-:12])=[O:11])=[CH:3][C:2]([F:1])=[CH:7][N:6]=1

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 583186225-Fluoro-3-nitropicolinaldehyde

생성물 1

HCID 583186012-(1,3-Dioxolan-2-yl)-5-fluoro-3-nitropyridine

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
120 °C

실험 절차

To a solution of 5-fluoro-3-nitropicolinaldehyde (12.5 g, 73.48 mmol) in toluene (220 mL) were added p-toluene sulfonic acid (698 mg, 3.67 mmol) and ethylene glycol (20.7 mL, 367.43 mmol) at 25° C. The reaction mixture was heated to 120° C. for overnight and water was removed using dean-stark apparatus. Reaction mass was cooled to 25° C. Water was added to the reaction mass and extracted with EtOAc. Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated in vacuo and purified by column chromatography on silica gel using 0-10% EtOAc in hexane to give 2-(1,3-dioxolan-2-yl)-5-fluoro-3-nitropyridine: 1H NMR (400 MHz, DMSO-d6): δ 4.02 (s, 4H), 6.22 (s, 1H), 8.939 (d, 1H, J=1.2 Hz); LC-MS (ESI) m/z 215.1 [M+H]+.

후처리

  1. customwater was removed
  2. customReaction mass
  3. temperaturewas cooled to 25° C
  4. extractionextracted with EtOAc
  5. washOrganic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe organic layer was concentrated in vacuo
  8. custompurified by column chromatography on silica gel using 0-10% EtOAc in hexane

출처 및 근거

ORD 기록
ord-8e91ba4c650748a5ab4f680fca55035b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633313B2

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