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

HRID 75510

반응식

HRID 75510 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebf9e313d559476a8fb1a6ce9712deae
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835444B2

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