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

HRID 536090노트

반응식

HRID 536090 반응식
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]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium Carbonate2회HCID 12341Ethane, 1-chloro-2-ethoxy-2회HCID 707192-Methylpyridin-3-ol

생성물 1

HCID 670684753-(2-Ethoxyethoxy)-2-methylpyridine수율 75%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-03fed8b67ae14aaebbaee8f5a82c3451
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859568B2

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