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

HRID 1666397
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HRID 1666397 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][CH:10]=[CH:9][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:12]1[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])=[N:8][CH:9]=[CH:10][CH:11]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 31215Triethyl phosphiteHCID 668763822-(3-(Chloromethyl)phenoxy)-3-methylpyridine

생성물 1

HCID 86623901Diethyl 3-(3-methylpyridin-2-yloxy)benzylphosphonate수율 85.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
150 °C

실험 절차

2-(3-(Chloromethyl)phenoxy)-3-methylpyridine (3.6 g, 15 mmol) from Step 2 was treated neat with triethylphosphite (3.3 mL, 19.3 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 (4.3 g, 83% 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-4b449c9c88d84ec3a351a06a4b177a56
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08044052B2

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