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

HRID 473424ノート

反応式

HRID 473424 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-8e91ba4c650748a5ab4f680fca55035b
出典データセット
uspto-grants-2014_01
特許番号
US08633313B2

反応ノート

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