Pyridine → 4-(4-Isopropoxyphenoxy)benzaldehyde

HRID 404879

反応式

HRID 404879 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 877217474-(4-Isopropoxyphenoxy)benzaldehyde収率 56.2%

試薬・触媒・溶媒 2

HCID 164827Copper oxide (CuO)触媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-d9dd6c9633f04085bc54f055c08be427
出典データセット
uspto-grants-2014_06
特許番号
US08748627B2

関連ノート

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