Phosphorus oxychloride → Ethyl 2-(2-chloropyridin-3-yl)acetate

HRID 481309

反応式

HRID 481309 の反応式
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N+:8]([O-])[CH:9]=[CH:10][CH:11]=1)[CH3:2].P(Cl)(Cl)([Cl:16])=O>>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[C:7]([Cl:16])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 42103603-Pyridineacetic acid, ethyl ester, 1-oxide

生成物 1

HCID 15326671Ethyl 2-(2-chloropyridin-3-yl)acetate収率 50%

実験手順

A mixture of 1.56 g (8.6 mol) of 3-pyridineacetic acid ethyl ester 1-oxide (for preparation, see A. R. Katritzky, J. Chem. Soc., 1956, 2404) and 15 ml of phosphorous oxychloride was heated to 80° C. for 3 hours. After cooling, the solvent was evaporated and the residue was poured onto ice water and solid sodium bicarbonate was added until the pH was basic. The organic layer was extracted with ethyl acetate and the combined extracts were dried over sodium sulfate and evaporated to an oil which was purified by flash chromatography with an ethyl acetate-hexane (1:4-1:1) eluant. The fractions containing the less polar isomer (Rf 0.3, ethyl acetate-hexane (3:7)) were combined and evaporated to yield 584 mg (50%) of the title compound of this preparation as an oil. 1H NMR (CDCl3): δ 1.22 (3H, t, J=7), 3.76 (2H, s), 4.15 (2H, q, J=7), 7.11-7.21 (2H, m), 8.25-8.31 (1H, m).

後処理

  1. customfor preparation
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. additionthe residue was poured onto ice water and solid sodium bicarbonate
  5. additionwas added until the pH
  6. extractionThe organic layer was extracted with ethyl acetate
  7. dry with materialthe combined extracts were dried over sodium sulfate
  8. customevaporated to an oil which
  9. customwas purified by flash chromatography with an ethyl acetate-hexane (1:4-1:1) eluant
  10. additionThe fractions containing the less polar isomer (Rf 0.3, ethyl acetate-hexane (3:7))
  11. customevaporated
  12. customto yield

出典と根拠

ORDレコード
ord-c6398db54f8d43fba5d136088495a66a
出典データセット
uspto-grants-1998_08
特許番号
US05789408

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