Water → 5-Nitro-2-(3-phenylpropoxy)pyridine

HRID 576069

반응식

HRID 576069 반응식
[H-].[Na+].[C:3]1([CH2:9][CH2:10][CH2:11][OH:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][N:15]=1.O>CN(C)C=O>[N+:20]([C:17]1[CH:18]=[CH:19][C:14]([O:12][CH2:11][CH2:10][CH2:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:15][CH:16]=1)([O-:22])=[O:21]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydride2회HCID 31234BenzenepropanolHCID 952642-Fluoro-5-nitropyridine

생성물 1

HCID 867072775-Nitro-2-(3-phenylpropoxy)pyridine수율 49.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

Sodium hydride (99 mg, 4.14 mmol) was added to a solution of 3-phenyl-1-propanol (564 μL, 4.14 mmol) in N,N-dimethylformamide (15 mL) while cooling in ice, and the mixture was stirred for 30 min while cooling in ice. A solution of 2-fluoro-5-nitropyridine (500 mg, 3.45 mmol) in N,N-dimethylformamide (5 mL) was added thereto. The mixture was warmed to room temperature and stirred for 19 hr. Subsequently, sodium hydride (99 mg, 4.14 mmol) was added thereto and the mixture was stirred at room temperature for 2 hr. Thereafter, the mixture was heated to 85° C., stirred for 1.5 hr, and further stirred at room temperature for 2 hr. Water was added to the reaction mixture while cooling in ice, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and dried over anhydrous magnesium sulfate. The desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1) to afford 5-nitro-2-(3-phenylpropoxy)pyridine as a brown solid (440 mg).

후처리

  1. temperaturewhile cooling in ice
  2. temperaturewhile cooling in ice
  3. stirringstirred for 19 hr
  4. stirringthe mixture was stirred at room temperature for 2 hr
  5. temperatureThereafter, the mixture was heated to 85° C.
  6. stirringstirred for 1.5 hr
  7. stirringfurther stirred at room temperature for 2 hr
  8. temperaturewhile cooling in ice
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with 1 mol/L hydrochloric acid
  11. dry with materialdried over anhydrous magnesium sulfate
  12. filtrationThe desiccant was filtered off
  13. concentrationfollowed by concentration under reduced pressure
  14. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1)

출처 및 근거

ORD 기록
ord-ce5a4ca8ec8d4a5a8075a60b722f6e62
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035059B2

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