Cesium carbonate → 2,3-Dichloro-5-(2,2-diethoxyethoxy)pyridine

HRID 81622

反応式

HRID 81622 の反応式
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5]Br)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C(=O)C.[Cl:22][C:23]1[CH:24]=[C:25]([OH:30])[CH:26]=[N:27][C:28]=1[Cl:29]>C(OCC)(=O)C>[Cl:29][C:28]1[C:23]([Cl:22])=[CH:24][C:25]([O:30][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[CH:26][N:27]=1

参加物

6

反応物 4

HCID 10796Cesium carbonateHCID 31374DimethylacetamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 143916722,3-Dichloro-5-hydroxypyridine

生成物 1

HCID 866458962,3-Dichloro-5-(2,2-diethoxyethoxy)pyridine収率 88.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Bromoacetaldehyde diethyl acetal (2.74 ml, 18.3 mmol) and cesium carbonate (9.93 g, 30.5 mmol) were added to an N,N-dimethylacetamide solution (10 ml) of 5,6-dichloropyridin-3-ol (1.0 g, 6.10 mmol), and stirred under a nitrogen atmosphere at 100° C. for 16 hours. Saline solution and ethyl acetate were added to the reaction solution, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=11:1 to 9:1) to obtain 2,3-dichloro-5-(2,2-diethoxyethoxy)pyridine (1.51 g, yield: 88%) as an orange oil.

後処理

  1. washthe organic layer was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate=11:1 to 9:1)

出典と根拠

ORDレコード
ord-499267f0d56448ea863eca0a72cb2f61
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

関連ノート

読み込み中…