Dimethylformamide → 5-[2-(1,3-Dioxolan-2-yl)ethoxy]-2,3-difluoropyridine

HRID 1517278ノート

反応式

HRID 1517278 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1.CN(C)C=O.[F:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[N:25][C:26]=1[F:27]>O>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[CH2:9][CH2:8][O:28][C:23]1[CH:22]=[C:21]([F:20])[C:26]([F:27])=[N:25][CH:24]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 684308605,6-Difluoropyridin-3-ol

生成物 1

HCID 684297625-[2-(1,3-Dioxolan-2-yl)ethoxy]-2,3-difluoropyridine収率 38.1%

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 (33 g, 100 mmol) and 2-(2-bromoethyl)-1,3-dioxolane (12 g, 67 mmol) were added to an N,N-dimethylformamide suspension (30 ml) of 5,6-difluoropyridin-3-ol (8.8 g, 67 mmol), and stirred at 100° C. for 1 hour. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:chloroform=1:1 to 0:1) to obtain 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2,3-difluoropyridine (5.9 g, yield: 38%) as a pale yellow 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 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:chloroform=1:1 to 0:1)

出典と根拠

ORDレコード
ord-d4c0287df12441738b873d1c079941c1
出典データセット
uspto-grants-2012_07
特許番号
US08232284B2

反応ノート

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