Water → 3-(2-Ethoxyethoxy)-2-methylpyridine

HRID 536090ノート

反応式

HRID 536090 の反応式
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1.[CH2:15]([O:17][CH2:18][CH2:19]Cl)[CH3:16].O>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:17][CH2:18][CH2:19][O:7][C:8]1[C:9]([CH3:14])=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:16]

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium Carbonate2 回HCID 12341Ethane, 1-chloro-2-ethoxy-2 回HCID 707192-Methylpyridin-3-ol

生成物 1

HCID 670684753-(2-Ethoxyethoxy)-2-methylpyridine収率 75%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

Potassium carbonate (2.20 g, 15.9 mmol) was added to a stirred solution of 3-hydroxy-2-methylpyridine (1.45 g, 13.3 mmol) and 2-chloroethyl ethyl ether (1.75 mL, 15.9 mmol) in DMF (7 mL) and the mixture was stirred at 70° C. overnight. The reaction was not complete and additional 2-chloroethyl ethyl ether (1 equiv.) and potassium carbonate (1 equiv.) were added and the mixture was stirred at 85° C. for 8 h. Water and ethyl acetate were added and the aqueous layer was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and concentrated. The crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate), obtaining 1.80 g (75%) the title compound.

後処理

  1. stirringthe mixture was stirred at 85° C. for 8 h
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (heptane/ethyl acetate gradient; 0 to 50% ethyl acetate)

出典と根拠

ORDレコード
ord-03fed8b67ae14aaebbaee8f5a82c3451
出典データセット
uspto-grants-2014_10
特許番号
US08859568B2

反応ノート

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