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

HRID 81664ノート

反応式

HRID 81664 の反応式
[CH3:1][O:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:12][C:13]1[CH:14]=[C:15]([OH:20])[CH:16]=[N:17][C:18]=1[Cl:19].O.[Cl-].[NH4+]>C(OCC)(=O)C.CN(C)C(=O)C>[Cl:19][C:18]1[C:13]([Cl:12])=[CH:14][C:15]([O:20][CH2:4][CH2:3][O:2][CH3:1])=[CH:16][N:17]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 143916722,3-Dichloro-5-hydroxypyridineHCID 57429219Ammonium chloride monohydrate

生成物 1

HCID 866459022,3-Dichloro-5-(2-methoxyethoxy)pyridine収率 85%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
80 °C

実験手順

2-Bromoethyl methyl ether (0.44 ml, 4.57 mmol) and cesium carbonate (2.48 g, 7.62 mmol) were added to an N,N-dimethylacetamide solution (5 ml) of 5,6-dichloropyridin-3-ol (500 mg, 3.05 mmol), and stirred under a nitrogen atmosphere at 80° C. for 5 hours. The reaction solution was cooled with ice, then ammonium chloride water and ethyl acetate were added, 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=9:1) to obtain 2,3-dichloro-5-(2-methoxyethoxy)pyridine (573 mg, yield: 85%) as an orange oil.

後処理

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

出典と根拠

ORDレコード
ord-32deaa2d4ebe4137b2c57faecb2d6491
出典データセット
uspto-grants-2014_09
特許番号
US08846700B2

反応ノート

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