Pyridine → 4-(4-Isopropoxyphenoxy)benzaldehyde

HRID 404879

반응식

HRID 404879 반응식
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].Br[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].N1C=CC=CC=1>[O-2].[Cu+2].ClCCl>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

참가 물질

7

반응물 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 820014-Isopropoxyphenol

생성물 1

HCID 877217474-(4-Isopropoxyphenoxy)benzaldehyde수율 56.2%

시약·촉매·용매 2

HCID 164827Copper oxide (CuO)촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of Example 17A (1.50 g, 9.86 mmol), 4-bromobenzaldehyde (2.20 g, 11.9 mmol.), (K2CO3 (2.85 g, 20.6 mmol) and pyridine (50 mL) at 80° C. was added Cu(II) oxide (1.95 g, 24.5 mmol). After the addition, the mixture was refluxed vigorously for 20 hours. After cooling, dichloromethane was added and the mixture was filtered through Celite. The filtrate was concentrated to dryness. The residue was dissolved in ether, which was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×), dried over MgSO4, and concentrated to dryness. The residue was purified on silica gel eluting with a hexane and ethyl acetate gradient to give the desired product as a white solid (1.42 g, 56%).

후처리

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed vigorously for 20 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered through Celite
  5. concentrationThe filtrate was concentrated to dryness
  6. dissolutionThe residue was dissolved in ether
  7. washwhich was washed with 10% HCl (2×), 1N NaOH (2×), brine (1×)
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated to dryness
  10. customThe residue was purified on silica gel eluting with a hexane and ethyl acetate gradient

출처 및 근거

ORD 기록
ord-d9dd6c9633f04085bc54f055c08be427
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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