Dimethylformamide → 3-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine

HRID 81646

反応式

HRID 81646 の反応式
[C:1](=O)([O-])[O-].[Cs+].[Cs+].BrC[CH2:9][CH:10]1O[CH2:13][CH2:12][O:11]1.CN(C)[CH:17]=[O:18].[Cl:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[N:25][C:26]=1[F:27]>O>[Cl:20][C:21]1[C:26]([F:27])=[N:25][CH:24]=[C:23]([O:28][CH2:9][CH:10]([O:18][CH2:17][CH3:1])[O:11][CH2:12][CH3:13])[CH:22]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 224515553-Chloro-2-fluoro-5-hydroxypyridine

生成物 1

HCID 684276023-Chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine収率 62%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Cesium carbonate (2.9 g, 8.9 mmol) and 2-(2-bromoethyl)-1,3-dioxolane (990 mg, 5.0 mmol) were added to an N,N-dimethylformamide suspension (10 ml) of 5-chloro-6-fluoropyridin-3-ol (570 mg, 3.9 mmol), and stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30) to obtain 3-chloro-5-(2,2-diethoxyethoxy)-2-fluoropyridine (640 mg, yield: 62%) as a colorless oil.

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated saline water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30)

出典と根拠

ORDレコード
ord-a35d61c75ba94b3e85d6a391a327ae05
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

関連ノート

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