Sodium Acetate → 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

HRID 324616ノート

反応式

HRID 324616 の反応式
C([O-])(=O)C.[Na+].Br[C:7]1[C:15]2[O:16][CH2:17][CH2:18][C:14]=2[C:13]2[C:12](=[O:19])[CH2:11][CH2:10][C:9]=2[C:8]=1Br.[H][H]>C(O)(=O)C.[C].[Pd]>[CH2:18]1[CH2:17][O:16][C:15]2[CH:7]=[CH:8][C:9]3[CH2:10][CH2:11][C:12](=[O:19])[C:13]=3[C:14]1=2

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 117272814,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 111376161,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one

試薬・触媒・溶媒 2

HCID 178418390HCID 178418390、化合物触媒HCID 176Acetic Acid溶媒

実験手順

5% Palladium carbon (50% hydrous, 2.9 g) and sodium acetate (17.9 g, 0.22 mol) were added to a solution of 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (29.0 g, 87.4 mmol) in acetic acid (550 ml), and the mixture was catalytically reduced in a hydrogen atmosphere at ordinary temperature and ordinary pressure. After absorption of the calculated amount of hydrogen, the palladium carbon was filtered off and the solvent was distilled off under reduced pressure. Water was added to the residue and the organic matter was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue obtained was purified by silica gel column chromatogarphy (ethyl acetate:hexane=15:85) to give the target compound. The yield was 13.5 g (89%).

後処理

  1. customAfter absorption of the calculated amount of hydrogen
  2. filtrationthe palladium carbon was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe organic matter was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materiala saturated aqueous sodium chloride solution and water and then dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue obtained
  10. customwas purified by silica gel column chromatogarphy (ethyl acetate:hexane=15:85)
  11. customto give the target compound

出典と根拠

ORDレコード
ord-5c49d59ab6644dfda6595af99d4ac77f
出典データセット
uspto-grants-2001_04
特許番号
US06218429B1

反応ノート

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