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

HRID 81622노트

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HRID 81622 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-499267f0d56448ea863eca0a72cb2f61
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846700B2

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