Ethanol → Ethyl 3-methylpyridine-2-carboxylate

HRID 1410782ノート

反応式

HRID 1410782 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-373a833ed31247cbba6c2ec6e800dbad
出典データセット
uspto-grants-2014_12
特許番号
US08921389B2

反応ノート

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