Water → Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonate

HRID 1666390노트

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HRID 1666390 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1.[CH2:17]([O:19][P:20]([O:24]CC)[O:21][CH2:22][CH3:23])[CH3:18].O>C(OCC)(=O)C>[CH3:13][C:9]1[N:8]=[C:7]([O:6][C:5]2[CH:4]=[C:3]([CH:16]=[CH:15][CH:14]=2)[CH2:2][P:20](=[O:24])([O:21][CH2:22][CH3:23])[O:19][CH2:17][CH3:18])[CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 668758892-(3-(Chloromethyl)phenoxy)-6-methylpyridine

생성물 1

HCID 86623900Diethyl 3-(6-methylpyridin-2-yloxy)benzylphosphonate수율 82.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

2-(3-(Chloromethyl)phenoxy)-6-methylpyridine (4.0 g, 17 mmol) from Step 2 was treated neat with triethylphosphite (3.67 mL, 21.4 mmol) and heated to 150° C. After 16 h, the reaction mixture was cooled to room temperature and partioned between water and ethyl acetate. The organic layer was separated and the aqueous was extracted again with ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (30-60%, EtOAc:CH2Cl2) to afford the title compound (4.7 g, 82% yield) as a thick oil.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted again with ethyl acetate
  4. dry with materialThe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (30-60%, EtOAc:CH2Cl2)

출처 및 근거

ORD 기록
ord-05252a3d0f22414cbd448bff218df469
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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