Ethanol → Ethyl 2-(3-chloropyridin-2-yl)propanoate

HRID 661373

反応式

HRID 661373 の反応式
[Cl:1][C:2]1[C:3]([CH:8]([CH3:11])[C:9]#N)=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.C(=O)(O)[O-:18].[Na+].[CH2:22]([OH:24])[CH3:23]>>[Cl:1][C:2]1[C:3]([CH:8]([CH3:11])[C:9]([O:24][CH2:22][CH3:23])=[O:18])=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 674989082-(3-Chloropyridin-2-yl)propanenitrile

生成物 1

HCID 67500197Ethyl 2-(3-chloropyridin-2-yl)propanoate収率 91%

反応条件

温度
0 °C

実験手順

The product of Example 38A (1.15 g, 6.9 mmol) was dissolved in absolute ethanol (14 mL) and cooled to 0° C. Concentrated sulfuric acid (13.54 g, 7.36 mL, 138 mmol) was added, and the reaction mixture was allowed to warm to ambient temperature. The reaction was then heated at reflux for 2 hours, cooled, and poured onto ice. The mixture was neutralized with saturated aqueous sodium bicarbonate, and extracted with two portions of ethyl acetate. The organic layers were separated and concentrated to give the title compound (1.34 g, 91%) which was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm8.49 (dd, J=1.5, 4.7, 1H), 7.93 (dd, J=1.5, 8.1, 1H), 7.36 (dd, J=4.7, 8.1, 1H), 4.29 (q, J=7.1, 1H), 4.07 (q, J=7.1, 2H), 1.42 (d, J=7.1, 3H), 1.11 (t, J=7.1, 3H). MS (DCI) m/z 214 (M+H)+.

後処理

  1. temperatureto warm to ambient temperature
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 2 hours
  4. temperaturecooled
  5. additionpoured onto ice
  6. extractionextracted with two portions of ethyl acetate
  7. customThe organic layers were separated
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a70969507a12430384c149df8c49f1ae
出典データセット
uspto-grants-2011_12
特許番号
US08084616B2

関連ノート

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