Benzyl 4-Hydroxybenzoate → Benzyl 4-(pyridin-3-yloxy)benzoate

HRID 1610600

반응식

HRID 1610600 반응식
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1>CN(C)C=O.[Cu]>[N:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:1][C:2]2[CH:17]=[CH:16][C:5]([C:6]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)[CH:26]=1

참가 물질

6

반응물 3

HCID 7180Benzyl 4-HydroxybenzoateHCID 122863-BromopyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 22262109Benzyl 4-(pyridin-3-yloxy)benzoate

시약·촉매·용매 2

HCID 23978Copper촉매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of benzyl 4-hydroxybenzoate (25.0 g, 110 mmol) in N,N-dimethylformamide (60 ml) was added potassium tert-butoxide (12.3 g, 110 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction solution was evaporated under reduced pressure, and 3-bromopyridine (25.0 g, 110 mmol), a copper powder (1.76 g, 27.2 mmol) and N,N-dimethylformamide (80 ml) were added. The mixture was stirred at 120° C. for 8 hrs. The reaction solution was filtered with celite and the filtrate was evaporated under reduced pressure. To the residue was added water (500 ml) and the mixture was extracted with ethyl acetate (500 ml). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1) to give the objective substance (18.0 g, 54%, crude).

후처리

  1. stirringThe mixture was stirred at 120° C. for 8 hrs
  2. filtrationThe reaction solution was filtered with celite
  3. customthe filtrate was evaporated under reduced pressure
  4. additionTo the residue was added water (500 ml)
  5. extractionthe mixture was extracted with ethyl acetate (500 ml)
  6. washThe extract was washed successively with water and saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1-2:1)
  10. customto give the objective substance (18.0 g, 54%, crude)

출처 및 근거

ORD 기록
ord-3fadcb0b6113453aac7fa19ac40d1eab
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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