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

HRID 1666390ノート

反応式

HRID 1666390 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-05252a3d0f22414cbd448bff218df469
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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