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

HRID 1610600

反応式

HRID 1610600 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3fadcb0b6113453aac7fa19ac40d1eab
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

関連ノート

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