Ethanol → Ethyl 3-methylpyridine-2-carboxylate

HRID 919779ノート

反応式

HRID 919779 の反応式
[CH3:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15][CH2:16]O>>[CH2:15]([O:9][C:8]([C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])[CH3:16]

参加物

4

反応物 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 2687573-Methylpicolinic acid

生成物 1

HCID 12243768Ethyl 3-methylpyridine-2-carboxylate

反応条件

温度
-20 °C

実験手順

3-Methyl-pyridine-2-carboxylic acid (1 g, 7.29 mmol) was dissolved in EtOH (50 mL) and cooled to −20° C. Thionyl chloride (1.1 mL, 14.6 mmol) was added, and the resulting white suspension was refluxed for 5 h, then concentrated to dryness. Water (10 mL) was added and solid Na2CO3 was added to neutralize the solution. The resulting mixture was extracted with ether. The organic layer was dried over MgSO4, and the solvent was removed by distillation to give 1.25 g of the title compound as an oil. 1H NMR (CDCl3, 200 MHz): δ=8.54 (d, 1H, J=3.9 Hz), 7.59 (d, 1H, J=7.8 Hz), 7.26-7.40 (m, 1H), 4.45 (q, 2H, J=7.0 Hz), 2.59 (s, 3H), 1.45 (t, 3H, J=7.0 Hz).

後処理

  1. temperaturethe resulting white suspension was refluxed for 5 h
  2. concentrationconcentrated to dryness
  3. additionWater (10 mL) was added
  4. additionsolid Na2CO3 was added
  5. extractionThe resulting mixture was extracted with ether
  6. dry with materialThe organic layer was dried over MgSO4
  7. customthe solvent was removed by distillation

出典と根拠

ORDレコード
ord-cdaa3a4ca20c4a21bc6fb50c2f1481f4
出典データセット
uspto-grants-2016_03
特許番号
US09271970B2

反応ノート

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