Water → (2-oxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetic Acid

HRID 488864ノート

反応式

HRID 488864 の反応式
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.C(N(CC)CC)C.C([CH:28]([CH2:32][C:33](Cl)=[O:34])[C:29](Cl)=[O:30])C.[OH2:36]>C1COCC1>[O:34]=[C:33]1[C:32]([CH2:28][C:29]([OH:30])=[O:36])=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:3]2[C:2](=[CH:10][C:9]3[CH2:8][CH2:7][CH2:6][C:5]=3[CH:4]=2)[O:1]1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 10823834(6-hydroxy-2,3-dihydro-1H-inden-5-yl)(phenyl)methanoneHCID 218646082-Ethylbutanedioyl dichloride

生成物 1

HCID 22267228(2-oxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetic Acid収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (6-hydroxy-2,3-dihydro-1H-inden-5-yl)(phenyl)methanone (1.0 g) and triethylamine (0.98 ml) in THF (20 ml) was combined with ethyl succinyl chloride (0.55 ml) at 0° C., and stirred for 1 hour. The reaction solution was combined with water, and the product was extracted with ethyl acetate. The extract was washed with a 1 N solution of hydrochloric acid followed by a saturated aqueous solution of sodium chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure. The resultant residue was dissolved in toluene (10 ml), combined with DBU (0.25 ml), and heated under reflux for 2.5 hours. After cooling, the reaction solution was diluted with ethyl acetate (60 ml), and washed with water followed by a 1 N solution of hydrochloric acid and a saturated aqueous solution of sodium chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:2). The resultant crude product of ethyl (2-oxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetate was dissolved in acetic acid (20 ml) and concentrated hydrochloric acid (10 ml), and heated under reflux for 1 hour. The reaction solution was concentrated under reduced pressure, and the resultant residue was dissolved in a solvent mixture of THF (5 ml) and ethyl acetate (50 ml), and then washed with water followed by a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by recrystallization from ethyl acetate-isopropyl ether to obtain the title compound (0.95 g, yield: 70%).

後処理

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with a 1 N solution of hydrochloric acid
  3. dry with materialAfter drying over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. dissolutionThe resultant residue was dissolved in toluene (10 ml)
  6. temperatureheated
  7. temperatureunder reflux for 2.5 hours
  8. temperatureAfter cooling
  9. additionthe reaction solution was diluted with ethyl acetate (60 ml)
  10. washwashed with water
  11. dry with materialAfter drying over magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customthe residue was purified by a column chromatography (packing: silica gel, eluent: ethyl acetate-hexane=1:2)
  14. dissolutionThe resultant crude product of ethyl (2-oxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetate was dissolved in acetic acid (20 ml)
  15. temperatureconcentrated hydrochloric acid (10 ml), and heated
  16. temperatureunder reflux for 1 hour
  17. concentrationThe reaction solution was concentrated under reduced pressure
  18. dissolutionthe resultant residue was dissolved in a solvent mixture of THF (5 ml) and ethyl acetate (50 ml)
  19. washwashed with water
  20. dry with materialAfter drying over magnesium sulfate
  21. distillationthe solvent was distilled off under reduced pressure
  22. customthe residue was purified by recrystallization from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-b7e249cbb5384359bed85d85491a89d5
出典データセット
uspto-grants-2005_12
特許番号
US06974806B2

反応ノート

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