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Tetrahydrofuran → (E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enal

HRID 36918
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HRID 36918 반응식
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](C=O)=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=[C:12]([O:21][CH3:22])[C:11]=2[CH2:23][O:24][CH3:25])=[CH:6][CH:5]=1.O.O.C(O)(=O)C(O)=O.[O:34]1C[CH2:37][CH2:36][CH2:35]1>O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](/[CH:37]=[CH:36]/[CH:35]=[O:34])=[C:14]([CH:18]([CH3:20])[CH3:19])[N:13]=[C:12]([O:21][CH3:22])[C:11]=2[CH2:23][O:24][CH3:25])=[CH:6][CH:5]=1
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참가 물질

6

반응물 4

HCID 8028Tetrahydrofuran3회HCID 24758Sodium hydrideHCID 61373Oxalic acid dihydrateHCID 199366934-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridine-5-carbaldehyde

생성물 1

HCID 19936689(E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enal

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

804 (3.1 mmol) of diethyl 2-(cyclohexylamino)-vinyl-phosphate dissolved in 6 ml of dry tetrahydrofuran are added dropwise under nitrogen to a suspension of 59 mg (2.5 mmol) of sodium hydride in 6 ml of dry tetrahydrofuran at -5° C. After 30 min, 0.65 g (2.05 mmol) of the compound from Example 9 in 15 ml of dry tetrahydrofuran is added dropwise at the same temperature and the mixture is heated to reflux for 30 min. After cooling to room temperature, the mixture is added to 200 ml of ice-cold water and extracted three times using 100 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. After concentration in vacuo, the residue is taken up in 5 ml of toluene, treated with a solution of 0.9 g (7 mmol) of oxalic acid dihydrate in 12 ml of water and heated to reflux for 90 min. After cooling to room temperature, the phases are separated, and the organic phase is washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo. The residue is dissolved in methylene chloride and filtered through silica gel.

후처리

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 30 min
  3. extractionextracted three times
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationAfter concentration in vacuo
  7. temperatureheated
  8. temperatureto reflux for 90 min
  9. temperatureAfter cooling to room temperature
  10. customthe phases are separated
  11. washthe organic phase is washed with saturated sodium chloride solution
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated in vacuo
  14. dissolutionThe residue is dissolved in methylene chloride
  15. filtrationfiltered through silica gel

출처 및 근거

ORD 기록
ord-71320257f16b4873a998fad0d7a02c00
출처 데이터셋
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05418243

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