Acetone → 1-(Pyridin-3-yl)butane-1,3-dione

HRID 75510

反応式

HRID 75510 の反応式
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].[CH3:14][C:15]([CH3:17])=[O:16].Cl>C1COCC1>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1](=[O:9])[CH2:14][C:15](=[O:16])[CH3:17])[CH:3]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 69188Ethyl Nicotinate

生成物 1

HCID 3001601-(Pyridin-3-yl)butane-1,3-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A cooled (0° C.) solution of ethyl nicotinate (3.00 g, 2.71 ml, 19.65 mmol) in THF (10 ml) was treated with sodium hydride (60%, 1.572 g, 39.3 mmol) followed by the dropwise addition of a solution of acetone (2.282 g, 39.3 mmol, 2.89 ml) in THF (10 ml). The mixture was heated at reflux for 3 hours and then allowed to cool to RT. The mixture was acidified to ˜pH5 with 2M HCl and partitioned between EtOAc and water. The organic phase was separated and washed with water, brine, dried (MgSO4) filtered and the solvent was removed in vacuo. Purification by chromatography on silica eluting with iso-hexane/EtOAc afforded the titled compound; 1H NMR (CDCl3, 400 MHz) δ 15.97 (1H, s), 9.10 (1H, s), 8.78 (1H, d), 8.22 (1H, d), 7.49 (1H, t), 6.21 (1H, s), 2.25 (3H, s). LCMS Rt=1.13 mins; [M+H]+ 164.21 Method LowpH_v002.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. custompartitioned between EtOAc and water
  4. customThe organic phase was separated
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customPurification by chromatography on silica eluting with iso-hexane/EtOAc

出典と根拠

ORDレコード
ord-ebf9e313d559476a8fb1a6ce9712deae
出典データセット
uspto-grants-2014_09
特許番号
US08835444B2

関連ノート

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